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CHI - BOS

$27 Find cheap flights from Chicago to Boston

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Boston departing on 9/25. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Fri 6/14
Fri 6/21

Search hundreds of travel sites at once for deals on flights to Boston

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Boston.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Boston.
In the last 7 days travelers have searched 42,393,389 times on KAYAK, and here is why:

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Cheap flight deals from Chicago to Boston (CHI-BOS)

 
These are the cheapest deals for flights from Chicago to Boston currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Chicago to Boston

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to Boston.

Recent one-way flight deals from Chicago to Boston

Only flying one-way? Below are some of the best one-way flight deals from Chicago to Boston found on KAYAK recently.

Recent last minute flight deals from Chicago to Boston

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Chicago to Boston.

Recent direct flight deals from Chicago to Boston

The latest deals for direct flights from Chicago to Boston so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Chicago to Boston

Find recent round-trip train or bus tickets from Chicago to Boston.

All round-trip flight deals to Boston

The cheapest plane tickets to Boston found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
8:02 pm - 11:31 pmORD-BOS
2h 29mnonstop
6:30 am - 8:24 amBOS-ORD
2h 54mnonstop
$55Spirit Airlines
Find Deal
Wed, Jun 5 - Sat, Jun 8
8:02 pm - 11:31 pmORD-BOS
2h 29mnonstop
6:30 am - 8:24 amBOS-ORD
2h 54mnonstop
$62Spirit Airlines
Find Deal
Wed, Jun 5 - Sat, Jun 8
9:04 pm - 12:22 amORD-BOS
2h 18mnonstop
7:00 am - 8:33 amBOS-ORD
2h 33mnonstop
$63Spirit Airlines
Find Deal
Fri, Sep 6 - Fri, Sep 13
6:00 am - 9:18 amORD-BOS
2h 18mnonstop
5:15 am - 7:10 amBOS-ORD
2h 55mnonstop
$147American Airlines
Find Deal
Sat, Aug 10 - Wed, Aug 28
10:35 am - 8:07 pmORD-BOS
8h 32m1 stop
6:12 am - 9:51 amBOS-ORD
4h 39m1 stop
$156JetBlue
Find Deal
Fri, Jul 5 - Tue, Jul 9
12:55 pm - 4:26 pmORD-BOS
2h 31mnonstop
6:25 am - 8:20 amBOS-ORD
2h 55mnonstop
$163Delta
Find Deal
Sat, Jun 1 - Tue, Jun 4
10:37 am - 8:02 pmORD-BOS
8h 25m1 stop
5:15 am - 9:51 amBOS-ORD
5h 36m1 stop
$166JetBlue
Find Deal
Sat, Aug 10 - Wed, Aug 28
6:30 am - 12:14 pmORD-BOS
4h 44m1 stop
5:25 am - 7:21 amBOS-ORD
2h 56mnonstop
$196American Airlines
Find Deal
Fri, May 31 - Tue, Jun 4
6:04 am - 9:24 amORD-BOS
2h 20mnonstop
5:45 am - 9:43 amBOS-ORD
4h 58m1 stop
$199United Airlines
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Thu, May 30 - Sun, Jun 2
9:32 am - 5:45 pmMDW-BOS
7h 13m1 stop
11:40 am - 9:06 amBOS-MDW
22h 26m2 stops
$310Delta
Find Deal
Tue, Jun 4 - Wed, Jun 5
9:04 pm - 12:22 amORD-BOS
2h 18mnonstop
$27Spirit Airlines
Find Deal
Wed, Sep 25
9:10 pm - 12:38 amORD-BOS
2h 28mnonstop
$31Spirit Airlines
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Thu, Jun 13
8:00 am - 11:12 amORD-BOS
2h 12mnonstop
$79Delta
Find Deal
Sat, Aug 17
10:35 am - 8:07 pmORD-BOS
8h 32m1 stop
$84JetBlue
Find Deal
Wed, Jul 3
3:42 pm - 9:48 pmORD-BOS
5h 06m1 stop
$88United Airlines
Find Deal
Sat, Aug 17
7:15 pm - 10:41 pmORD-BOS
2h 26mnonstop
$95JetBlue
Find Deal
Wed, May 29
8:10 pm - 11:46 pmORD-BOS
2h 36mnonstop
$104Delta
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Fri, May 31
4:35 pm - 10:54 pmORD-BOS
5h 19m1 stop
$108United Airlines
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Sat, May 25
8:29 pm - 11:55 pmORD-BOS
2h 26mnonstop
$115American Airlines
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Thu, May 30
6:30 am - 12:14 pmORD-BOS
4h 44m1 stop
$128American Airlines
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Tue, May 21
5:56 pm - 9:43 amORD-BOS
14h 47m1 stop
11:42 am - 12:58 amBOS-ORD
14h 16m1 stop
$136Frontier
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Sat, May 18 - Sat, Jun 1
9:08 pm - 9:43 amMDW-BOS
11h 35m1 stop
11:42 am - 6:54 amBOS-MDW
20h 12m1 stop
$136Frontier
Find Deal
Sat, May 18 - Sat, Jun 1
9:08 pm - 9:43 amMDW-BOS
11h 35m1 stop
12:59 pm - 7:57 pmBOS-MDW
7h 58m1 stop
$150Frontier
Find Deal
Sat, May 18 - Sat, May 25
4:53 pm - 11:30 pmORD-BOS
5h 37m1 stop
5:25 am - 7:21 amBOS-ORD
2h 56mnonstop
$249American Airlines
Find Deal
Mon, May 20 - Mon, May 27
10:45 am - 6:25 pmORD-BOS
6h 40m1 stop
6:10 am - 8:04 amBOS-ORD
2h 54mnonstop
$257JetBlue
Find Deal
Mon, May 20 - Mon, May 27
10:45 am - 6:25 pmORD-BOS
6h 40m1 stop
5:45 am - 9:56 amBOS-ORD
5h 11m1 stop
$267JetBlue
Find Deal
Mon, May 20 - Tue, May 28
4:53 pm - 11:30 pmORD-BOS
5h 37m1 stop
6:05 am - 8:18 amBOS-ORD
3h 13mnonstop
$274American Airlines
Find Deal
Mon, May 20 - Sat, May 25
6:27 am - 9:54 amORD-BOS
2h 27mnonstop
8:05 am - 10:03 amBOS-ORD
2h 58mnonstop
$283Delta
Find Deal
Fri, May 17 - Sun, May 26
1:32 pm - 8:12 pmORD-BOS
5h 40m1 stop
8:05 am - 10:03 amBOS-ORD
2h 58mnonstop
$292Delta
Find Deal
Fri, May 17 - Sun, May 26
7:15 am - 10:38 amORD-BOS
2h 23mnonstop
5:45 am - 9:35 amBOS-ORD
4h 50m1 stop
$336United Airlines
Find Deal
Sun, May 19 - Tue, May 28
8:02 pm - 11:31 pmORD-BOS
2h 29mnonstop
6:30 am - 8:24 amBOS-ORD
2h 54mnonstop
$55Spirit Airlines
Find Deal
Wed, Jun 5 - Sat, Jun 8
8:02 pm - 11:31 pmORD-BOS
2h 29mnonstop
6:30 am - 8:24 amBOS-ORD
2h 54mnonstop
$62Spirit Airlines
Find Deal
Wed, Jun 5 - Sat, Jun 8
8:10 pm - 11:46 pmORD-BOS
2h 36mnonstop
6:25 am - 8:20 amBOS-ORD
2h 55mnonstop
$137Delta
Find Deal
Fri, May 31 - Tue, Jun 4
6:00 am - 9:18 amORD-BOS
2h 18mnonstop
5:15 am - 7:10 amBOS-ORD
2h 55mnonstop
$147American Airlines
Find Deal
Sat, Aug 10 - Wed, Aug 28
6:00 am - 9:18 amORD-BOS
2h 18mnonstop
7:30 pm - 9:26 pmBOS-ORD
2h 56mnonstop
$157American Airlines
Find Deal
Sat, Aug 10 - Sat, Aug 17
12:55 pm - 4:26 pmORD-BOS
2h 31mnonstop
6:25 am - 8:20 amBOS-ORD
2h 55mnonstop
$163Delta
Find Deal
Sat, Jun 1 - Tue, Jun 4
8:33 pm - 11:59 pmORD-BOS
2h 26mnonstop
6:00 am - 7:54 amBOS-ORD
2h 54mnonstop
$167JetBlue
Find Deal
Tue, Jul 2 - Sat, Jul 6
6:04 am - 9:24 amORD-BOS
2h 20mnonstop
3:19 pm - 5:10 pmBOS-ORD
2h 51mnonstop
$172United Airlines
Find Deal
Tue, Jun 18 - Tue, Jun 18
7:15 pm - 10:41 pmORD-BOS
2h 26mnonstop
4:25 pm - 6:20 pmBOS-ORD
2h 55mnonstop
$183JetBlue
Find Deal
Tue, May 28 - Sat, Jun 1
6:04 am - 9:24 amORD-BOS
2h 20mnonstop
6:00 am - 7:50 amBOS-ORD
2h 50mnonstop
$186United Airlines
Find Deal
Mon, May 27 - Thu, May 30
9:30 pm - 8:32 pmChicago Union-
Boston South Station
22h 02mnonstop
12:50 pm - 10:12 amBoston South Station-
Chicago Union
22h 22mnonstop
$150Amtrak
Find Deal
Sat, Jul 27 - Sat, Aug 3
9:30 pm - 8:24 pmChicago Union-
Boston Back Bay
21h 54mnonstop
12:57 pm - 10:12 amBoston Back Bay-
Chicago Union
22h 15mnonstop
$150Amtrak
Find Deal
Sat, Jul 27 - Sat, Aug 3
9:45 pm - 8:15 pmMilwaukee Badger-
Boston Allston
45h 30mnonstop
7:25 pm - 10:05 amBoston Allston-
Milwaukee Badger
39h 40mnonstop
$222FlixBus
Find Deal
Tue, Jun 4 - Sat, Jun 8
4:30 pm - 10:55 amMilwaukee Badger-
Boston South Station
41h 25mnonstop
8:50 am - 5:05 pmBoston South Station-
Milwaukee Badger
33h 15mnonstop
$223FlixBus
Find Deal
Tue, Jun 4 - Sat, Jun 8
9:45 pm - 8:15 pmMilwaukee Badger-
Boston Allston
45h 30mnonstop
1:30 am - 5:05 pmBoston Allston-
Milwaukee Badger
40h 35mnonstop
$229FlixBus
Find Deal
Tue, Jun 4 - Fri, Jun 7
9:30 pm - 8:24 pmChicago Union-
Boston Back Bay
21h 54mnonstop
12:57 pm - 10:12 amBoston Back Bay-
Chicago Union
22h 15mnonstop
$301Amtrak
Find Deal
Sat, Jun 8 - Mon, Jun 10
9:30 pm - 8:24 pmChicago Union-
Boston Back Bay
21h 54mnonstop
12:57 pm - 10:12 amBoston Back Bay-
Chicago Union
22h 15mnonstop
$301Amtrak
Find Deal
Sat, Jun 8 - Mon, Jun 10
9:30 pm - 8:32 pmChicago Union-
Boston South Station
22h 02mnonstop
12:50 pm - 10:12 amBoston South Station-
Chicago Union
22h 22mnonstop
$301Amtrak
Find Deal
Sat, Jun 8 - Mon, Jun 10
9:30 pm - 8:32 pmChicago Union-
Boston South Station
22h 02mnonstop
12:50 pm - 10:12 amBoston South Station-
Chicago Union
22h 22mnonstop
$301Amtrak
Find Deal
Sat, Jun 8 - Mon, Jun 10
9:30 pm - 8:32 pmChicago Union-
Boston South Station
22h 02mnonstop
12:50 pm - 10:12 amBoston South Station-
Chicago Union
22h 22mnonstop
$318Amtrak
Find Deal
Thu, Jun 6 - Tue, Jun 11

Flights from Chicago to Boston - Travel Insights & Trends

Get data-powered insights and trends into flights from Chicago to Boston to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago to Boston flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Chicago to Boston.
Our data shows that the cheapest route for a one-way flight from Chicago to Boston cost $89 and was between Chicago O'Hare Intl Airport and Boston. On average, the best prices are found if you fly from Chicago Midway Airport to Boston. The average price for a return flight for this route is $129.

What’s the cheapest day of the week to fly from Chicago to Boston?

The average price of all flights from Chicago to Boston clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Boston on a Tuesday and more expensive on a Monday. On your return trip to Chicago, you should consider flying back on a Tuesday, and avoid Fridays for better deals.

What is the cheapest month to fly from Chicago to Boston?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Chicago to Boston, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Chicago to Boston is January, where tickets cost $201 on average. On the other hand, the most expensive months are June and July, where the average cost of tickets is $323 and $314 respectively.

How far in advance should I book a flight from Chicago to Boston?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago to Boston, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago to Boston, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 84 days before departure.

Which airlines provide the cheapest flights from Chicago to Boston?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the past 3 days, the cheapest one-way tickets to Boston from Chicago were found on Spirit Airlines ($27) and Frontier ($50), and the lowest round-trip tickets were found on Spirit Airlines ($55) and Frontier ($99).

Which airlines fly most frequently between Chicago and Boston?

Chicago and Boston are connected by different airlines. The airlines that fly that route the most regularly are American Airlines (11 flights per day), Southwest (9 flights per day), and Delta (8 flights per day).

Which airlines fly non-stop between Chicago and Boston?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Chicago to Boston.
There are 6 airlines that fly nonstop from Chicago to Boston. They are: American Airlines, Delta, JetBlue, Southwest, Spirit Airlines and United Airlines. The cheapest price of all airlines flying this route was found with Delta at $63 for a one-way flight. On average, the best prices for this route can be found at Spirit Airlines.

How many flights are there between Chicago and Boston per day?

Each day, there are between 37 and 45 nonstop flights that take off from Chicago and land in Boston, with an average flight time of 2h 25m. The most common departure time is 8:00 am and most flights take off in the morning. Each week, there are 297 flights. The most frequent day of departure is Thursday, when 15% of all weekly flights depart. The fewest flights depart on a Saturday.

Which cabin class options are there for flights between Chicago and Boston?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Chicago to Boston take?

The duration of a nonstop flight to Boston from Chicago is typically 2h 16m. The journey crosses a distance of 850 miles.

What’s the earliest departure time from Chicago to Boston?

Early birds can take the earliest flight from Chicago at 6:00 am and will be landing in Boston at 9:15 am.

What’s the latest departure time from Chicago to Boston?

If you prefer to fly at night, the latest flight from Chicago to Boston jets off at 9:45 pm and lands at 1:20 am.

Good to know

Low season

January

High season

October

Cheapest flight

$27
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Chicago O'Hare Airport to Boston

When to book flights from Chicago to Boston

Are your dates flexible? Find out the best times to travel from Chicago to Boston based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to Boston

  • How can I get to the Freedom Trail from Boston Logan International Airport (BOS)?

    The distance between the Freedom Trail and Boston Logan International Airport (BOS) is around 3.7 miles, and various transportation options run between the two points. Line 88 bus and the subway provide the best opportunity to travel between the two points, taking about 26min to cover the distance. However, a taxi is a quicker option, taking about 6min to get there.

  • Where are spas located at Boston Logan International Airport (BOS)?

    Travelers arriving in BOS from Chicago while weary can seek some therapy in one of the spas on this property. XpresSpa at Terminal B provides ideal services to help you relax and self-indulge. They include manicures, pedicures, facials, and deep-tissue massages.

  • Where can I withdraw money at Boston Logan International Airport (BOS)?

    If your wallet is depleted and you want to recharge it, you’ll find several ATMs at BOS run by numerous banks and credit unions. These ATMs are located throughout the airport terminals, pre-and post-security. For instance, Bank of America has its ATMs at the Arrivals Level, East End by Taxi Stand, Pre-Security.

  • What family-friendly amenities are at Boston Logan International Airport (BOS)?

    BOS caters to the needs of moms and the littlest family members through the provision of Mamava suites where lactating mothers can pump and breastfeed in privacy. You can locate one of them in Terminal E post-security in the Women's Restroom lobby.

  • Does Logan International Airport have pet relief areas?

    If you are traveling with a pet or service animal, make sure to stop by one of the pet relief areas in Logan International Airport after your flight has landed. There is a designated area conveniently located outside of the Arrivals doors for every terminal, and complimentary waste bags are provided for pet owners.

  • What are good hotels near Logan International Airport?

    The Hilton Boston Logan Airport is a chic, 4-star hotel that is directly connected to Logan International Airport via a skybridge and is less than a 7-minute drive from the Boston Common Park. The Hyatt Regency Boston Harbor is a standard option that is only a mile from the airport and a 5-minute drive from the famous Faneuil Hall.

  • What dining options are there in Chicago Midway International Airport?

    The Go Go White Sox Bar and Grill is located in the Central Market of Chicago Midway International Airport and serves classic American meals, while the Midway Pour House is in Concourse A and is known for having a variety of craft beers. Dunkin’ Donuts and Cafe Espresso are good options for travelers with little time that would like to purchase some to-go items.

  • Does Logan International Airport have a prayer room?

    Logan International Airport has the Our Lady of the Airways Chapel that is located in Terminal C of the Arrivals level. It is open during standard business hours and is available to all travelers, no matter what their spiritual affiliation is.

  • What is the cheapest flight from Chicago to Boston?

    In the last 3 days, the lowest price for a flight from Chicago to Boston was $27 for a one-way ticket and $55 for a round-trip.

  • Do I need a passport to fly between Chicago and Boston?

    A passport is not required to fly from Chicago to Boston.

  • Which airports will I be using when flying from Chicago to Boston?

    When flying out of Chicago you will be using one of these airports: Chicago Midway or Chicago O'Hare Intl. You will be landing at Boston Logan Intl.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to Boston?

    All the following airlines offer inflight Wi-Fi service on the Chicago to Boston flight route: American Airlines, JetBlue, Delta, British Airways, Finnair, and Iberia.

  • Which aircraft models fly most regularly from Chicago to Boston?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago to Boston flight route.

  • Which airline alliances offer flights from Chicago to Boston?

    oneworld, Star Alliance, and SkyTeam are the airline alliances operating flights between Chicago and Boston, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Chicago to Boston?

    There are nonstop flights from Chicago to Boston on a daily basis.

  • Which is the best airline for flights from Chicago to Boston, Delta or JetBlue?

    The two airlines most popular with KAYAK users for flights from Chicago to Boston are Delta and JetBlue. With an average price for the route of $263 and an overall rating of 8.0, Delta is the most popular choice. JetBlue is also a great choice for the route, with an average price of $234 and an overall rating of 7.6.

  • How does KAYAK find such low prices on flights from Chicago to Boston?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Boston.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Boston?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Boston from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Boston?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Boston with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Boston?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Boston from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding a cheap flight from Chicago to Boston

  • Looking for a cheap flight? 25% of our users found flights on this route for $139 or less one-way and $223 or less round-trip.
  • Travelers flying American Airlines from Chicago to Boston should remember that the airline’s hub is at Boston Logan International Airport (BOS). You’ll arrive through Terminal B, and the airline’s Admirals Club is located at the same terminal. Members and holders and registered cards enjoy unrestricted access to this amenity. However, Economy Class travelers can access it at a reduced cost.
  • If you’re departing to BOS via Chicago Midway International Airport (MDW), you’ll find a road system between the terminal and the secure area. Inter-terminal movement between the two buildings is through a pedestrian bridge. However, every traveler must be cleared at the security checkpoint in the terminal building on the way out to the concourse.
  • Suppose you’re flying aboard Delta Airlines from Chicago O’Hare International Airport (ORD) to Boston Logan International Airport (BOS). In that case, you’ll be glad to note that the carrier allows pets such as cats and dogs in the cabin. Nevertheless, your four-legged friends must bear certified vaccination certificates and relevant health licenses. Still, it would help if you confined them in their cages to prevent them from disturbing other passengers.
  • Chicago Midway International Airport (MDW) sits about 10.7 miles from Downtown Chicago, and several public transportation options travel between the two destinations. The most convenient commute from downtown Chicago to MDW is via the Orange Line train. The train regularly plies between the two points, covering the distance in approximately 20-25min.
  • Before your trip from Chicago to BOS, you might wish to have a private session with the Almighty. Those departing through ORD will be glad to know that this prayer suite is tucked away from the noisy terminals. The airport’s chapel lies on the Mezzanine level of Terminal 2, atop the Delta Air Lines ticket desk.
  • If you’re looking at flights from Chicago to Boston, there are two different airports that you can fly out of. O'Hare International Airport is the largest airport in the region and harbors a high concentration of flights, while Chicago Midway International Airport is a smaller choice that is located only several miles from the city’s downtown.
  • Hoping to have a direct flight from Chicago to Boston? There are several major airlines that you can choose from. Southwest Airlines is popular amongst travelers with a large amount of luggage, as they allow you to check up to two bags for free, while Delta Airlines offers many upgrade options for those who would prefer more comfortable chairs or extra legroom.
  • For those that are traveling with kids, make sure to stop by one of the several children’s play areas located in Logan International Airport. These play areas are free for all travelers and feature a variety of toys, games, and activities that will help kids (and their parents) unwind after a long day of traveling.
  • To help pass the time before your flight takes off from O'Hare International Airport, see if you can access one of the airport’s private lounges. American, United, and Delta Airlines all have lounges in Chicago, and they often provide complimentary or reduced price access passes for their customers.
  • Flying can sometimes be stressful, so make sure you’re taking the time to unwind before boarding your plane. O'Hare International Airport has both a fitness club and a yoga room, both of which are perfect ways to let off some steam and relax before embarking on a day of traveling.
See more tips

Prefer to fly non-stop from Chicago to Boston?

Find which airlines fly direct from Chicago to Logan Intl, which days they fly and book direct flights.

Nonstop departures

Chicago to Boston Logan Intl

Monday

ANA, Air New Zealand, Alaska Airlines, +21 more

ANA, Air New Zealand, +22 more

Tuesday

ANA, Air New Zealand, Alaska Airlines, +20 more

ANA, Air New Zealand, +21 more

Wednesday

ANA, Air New Zealand, Alaska Airlines, +22 more

ANA, Air New Zealand, +23 more

Thursday

ANA, Air New Zealand, Alaska Airlines, +21 more

ANA, Air New Zealand, +22 more

Friday

ANA, Air New Zealand, Alaska Airlines, +22 more

ANA, Air New Zealand, +23 more

Saturday

ANA, Air New Zealand, Alaska Airlines, +20 more

ANA, Air New Zealand, +21 more

Sunday

ANA, Air New Zealand, Alaska Airlines, +23 more

ANA, Air New Zealand, +24 more

See more direct flights

Nonstop returns

Boston Logan Intl to Chicago

Monday

ANA, Air New Zealand, Alaska Airlines, +22 more

ANA, Air New Zealand, +23 more

Tuesday

ANA, Air New Zealand, Alaska Airlines, +20 more

ANA, Air New Zealand, +21 more

Wednesday

ANA, Air New Zealand, Alaska Airlines, +22 more

ANA, Air New Zealand, +23 more

Thursday

ANA, Air New Zealand, Alaska Airlines, +22 more

ANA, Air New Zealand, +23 more

Friday

ANA, Air New Zealand, Alaska Airlines, +22 more

ANA, Air New Zealand, +23 more

Saturday

ANA, Air New Zealand, Alaska Airlines, +21 more

ANA, Air New Zealand, +22 more

Sunday

ANA, Air New Zealand, Alaska Airlines, +23 more

ANA, Air New Zealand, +24 more

See more direct flights
See more direct flights

Top 5 airlines serving from Chicago to Boston

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Boston. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Boston? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10691 reviews
7.9Comfort
8.6Crew
8.2Boarding
8.0Entertainment
7.4Food
Airline reviews

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

2.0 MediocreDevan, May 2024AUS - BOS
Read more about Delta reviews

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Atlanta boarding crew at gate were filled with arrogance and were disrespectful. In flight crew showed indifference to the needs of passengers. This is about the flight from ATL to BDL.

The boarding was horrible. You couldn’t hear the announcements at all. Probably because there is so much in the area for businesses. They need a louder PA system. Other than that it was a good Delta experience.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

Terrible. Delta delays caused us to miss our flight and they did nothing to fix it.

The A330-200 was showing its age but otherwise this was a pleasant flight with friendly crew. The meals/snack provided were pretty good.

The most unprofessional and disorganized experience I’ve ever had with an airlines. After the flight was diverted on the runway and we returned to the gate, there was no communication about the plans and it took an additional 5 hours to get set up with a hotel and a new flight, information that was not readily given to the passengers and mostly gotten second hand from what other passengers heard from each other. Based on this experience I cannot recommend flying delta again

Business class is great. New airplane, very comfortable, better than some of the major airlines I am used to

Delayed by almost an hour - I also noticed that all JetBlue flights departing from PBI were delayed yet the weather was perfect.

I loved the wifi, much better than Delta. Seats were old. and bathrooms dingy.

There was no wheelchair or wheelchair escort at the gate..unacceptable

Delayed 4 hours because of maintenance issue they knew about all day. Get another plane. Time is precious!

I liked that boarding and take off were timely despite a 15 minute delay due to weather. The pilot communicated with us the entire flight keeping us informed re: turbulance and slight delays on the runway after we landed.

Has been always great except flight cancelation in the past at very last minute waiting till 2am and we when have to beg for overnight accommodation

There were weather issues and coding problems whatever those refer to, but JetBlue, for two days in a row was unbelievably late. Several hours late, resulting in almost no sleep for passengers like me.

The plane was very hot. There were delays . Generally, the flight was great.

If jet blue is going to offer tv at every seat, fix the headphone connection so you can hear. Haven’t had a usable headphone jack in years

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Crew was great and did their best to make us comfortable and captain came out at the beginning to announce why the flight was delayed, weather situation up ahead, and kept us updated throughout the flight.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

Delayed abs delayed Gate crew giving poor info - we are definitely leaving at —- Ultimately to cancel flight after 4+ hours of delays Just cancel it earlier

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

This plane is my favorite despite the very limited overhead space. Seats are comfortable!

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Worst airline experience ever. Lost my IPad going thru security. Charged for my dog carriage at the gate not at ticket counter. Gave away my seat 6D. Expressed I wanted my seat back after charging me 99 for dog carriage. Should have thrown it out. Had a 16 yr old Yorkie heading to Boston after being a snowbird. Seats small. Very bad experience. Still don’t have my IPad. Horrible

Flight delayed then canceled! I will NEVER fly Spirit Airlines again and will tell all my friends!

Delayed..4 times...completely disorganized boarding. After 5 hours they scrambled to move ppl off plane bc they overbooked. Then they didn't have a cabin crew. WiFi on plane didn't work. Zero amenities. Once we boarded we sat on tarmac for an hour. Explore all alternate options including purchasing a pair of hiking boots and walking to your destination instead of flying spirit.

The seat was very uncomfortable from Boston to Nashville. Otherwise the flight was excellent.

I had a phobia for Spirit and now is 100% confirmed. Flight delayed, missed connecting flight and staying overnight . Now not even able to get my boarding pass until I’ll get into the airport. It’s really really bad at this point

the landing was terrible. the plane touched down and had take off. the plane flew around and landed a second time.i understand the weather might of been the problem. It was a scary experience and no explanation from the captain.

The flight attendants were very personable, extremely friendly, and had a very good feeling of the energy around them not to mention they’re very funny and engaging. What made up for the discomfort of the seats and the fact that the plane sat for a long time on the Turmac. Not sure if the pilot was new, but the landing was very rough sort of like I was at a magic mountain theme park ride that was built in 1959

Flight was delayed 2+ hours missed a concert because of it…

Service was awesome 👍🙏 thank you Spirit Airlines...love the Big Seat...😎

Crew was very engaging and welcoming. Seat very uncomfortable and inadequate leg room made the trip a long 3 hours.

Book cheap flights from Chicago to Boston

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Boston found on KAYAK in the last 72 hours.
9/25Wed
nonstopSpirit Airlines
2h 18mORD-BOS
$27
6/13Thu
nonstopSpirit Airlines
2h 28mORD-BOS
$31
8/17Sat
nonstopDelta
2h 12mORD-BOS
$79
7/3Wed
1 stopJetBlue
8h 32mORD-BOS
$84
8/17Sat
1 stopUnited Airlines
5h 06mORD-BOS
$88
5/29Wed
nonstopJetBlue
2h 26mORD-BOS
$95
5/31Fri
nonstopDelta
2h 36mORD-BOS
$104
5/25Sat
1 stopUnited Airlines
5h 19mORD-BOS
$108
5/30Thu
nonstopAmerican Airlines
2h 26mORD-BOS
$115
5/21Tue
1 stopAmerican Airlines
4h 44mORD-BOS
$128

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Last minute flights from Chicago to Boston

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Boston that are departing in the next 10 days.
5/18Sat
multi-stopFrontier
14h 47mORD-BOS
6/1Sat
multi-stopFrontier
14h 16mBOS-ORD
$136
5/18Sat
multi-stopFrontier
11h 35mMDW-BOS
6/1Sat
multi-stopFrontier
20h 12mBOS-MDW
$136
5/18Sat
multi-stopFrontier
11h 35mMDW-BOS
5/25Sat
multi-stopFrontier
7h 58mBOS-MDW
$150
5/20Mon
multi-stopAmerican Airlines
5h 37mORD-BOS
5/27Mon
nonstopAmerican Airlines
2h 56mBOS-ORD
$249
5/20Mon
multi-stopJetBlue
6h 40mORD-BOS
5/27Mon
nonstopJetBlue
2h 54mBOS-ORD
$257
5/20Mon
multi-stopJetBlue
6h 40mORD-BOS
5/28Tue
multi-stopJetBlue
5h 11mBOS-ORD
$267
5/20Mon
multi-stopAmerican Airlines
5h 37mORD-BOS
5/25Sat
nonstopAmerican Airlines
3h 13mBOS-ORD
$274
5/17Fri
nonstopDelta
2h 27mORD-BOS
5/26Sun
nonstopDelta
2h 58mBOS-ORD
$283
5/17Fri
multi-stopDelta
5h 40mORD-BOS
5/26Sun
nonstopDelta
2h 58mBOS-ORD
$292
5/19Sun
nonstopUnited Airlines
2h 23mORD-BOS
5/28Tue
multi-stopUnited Airlines
4h 50mBOS-ORD
$336

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Flights to Boston

Destination:

Boston (BOS)United States

Return flight deals:

Boston - Chicago

Cabin classes:

$396
$403
$385
$129

Compare transportation modes for Chicago to Boston

Average priceAverage duration
Flights$9152h 15m
Trains$30221h 56m
Buses$22544h 08m