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HOU - CHI

$70 Find cheap flights from Houston Hobby Airport to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Hobby to Chicago departing on 6/3. 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
Thu 6/27
Thu 7/4

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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Houston to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Houston to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 42,816,550 times on KAYAK, and here is why:

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Cheap flight deals from Hobby to Chicago (HOU-CHI)

 
These are the cheapest deals for flights from Hobby to Chicago 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 Hobby to Chicago

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

Recent one-way flight deals from Hobby to Chicago

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

Recent last minute flight deals from Hobby to Chicago

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

Recent direct flight deals from Hobby to Chicago

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

Cheap bus & train deals from Hobby to Chicago

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

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
3:46 pm - 12:40 amHOU-ORD
8h 54m1 stop
9:53 pm - 8:53 amORD-HOU
11h 00m1 stop
$140Frontier
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Tue, Jun 11 - Wed, Jun 12
3:46 pm - 12:00 pmHOU-MDW
20h 14m1 stop
10:26 pm - 9:04 amMDW-HOU
10h 38m1 stop
$141Frontier
Find Deal
Tue, Jun 11 - Sat, Jun 15
7:19 pm - 7:08 amHOU-ORD
11h 49m1 stop
7:13 pm - 8:17 pmORD-HOU
25h 04m1 stop
$141Frontier
Find Deal
Mon, Jun 10 - Thu, Jun 13
5:00 am - 10:05 amHOU-ORD
5h 05m1 stop
6:25 pm - 11:51 pmORD-HOU
5h 26m1 stop
$268American Airlines
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Sat, Jul 27 - Sat, Aug 3
5:00 am - 11:02 amHOU-ORD
6h 02m1 stop
8:40 am - 2:06 pmORD-HOU
5h 26m1 stop
$274American Airlines
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Tue, Jul 30 - Sat, Aug 3
7:18 pm - 11:59 pmHOU-ORD
4h 41m1 stop
11:19 am - 6:26 pmORD-HOU
7h 07m1 stop
$288Delta
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Tue, Sep 10 - Wed, Sep 11
7:00 am - 5:35 pmHOU-ORD
10h 35m1 stop
8:05 pm - 12:08 pmORD-HOU
16h 03m1 stop
$292Sun Country Air
Find Deal
Thu, Jul 4 - Sun, Jul 7
4:21 pm - 11:54 pmHOU-ORD
7h 33m1 stop
9:23 am - 3:31 pmORD-HOU
6h 08m1 stop
$317Delta
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Fri, Aug 2 - Sat, Aug 3
5:12 pm - 12:59 amHOU-ORD
7h 47m1 stop
7:00 am - 5:02 pmORD-HOU
10h 02m1 stop
Fri, Jul 19 - Sun, Jul 21
6:40 pm - 9:17 pmHOU-ORD
26h 37m2 stops
9:05 pm - 4:51 pmORD-HOU
19h 46m1 stop
Thu, Jun 13 - Sun, Jun 16
5:52 pm - 1:08 amHOU-ORD
7h 16m1 stop
$70Frontier
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Mon, Jun 3
7:19 pm - 7:08 amHOU-ORD
11h 49m1 stop
$76Frontier
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Mon, Jun 10
9:43 am - 12:40 amHOU-ORD
14h 57m1 stop
$77Frontier
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Thu, Jun 13
6:30 pm - 7:59 pmHOU-ORD
25h 29m1 stop
$125Sun Country Air
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Sun, Jul 28
6:27 pm - 11:41 pmHOU-ORD
5h 14m1 stop
$134American Airlines
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Sat, Jun 22
10:17 am - 2:55 pmHOU-MDW
4h 38m1 stop
$199Delta
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Mon, Jul 1
5:00 am - 9:55 amHOU-ORD
4h 55m1 stop
$216American Airlines
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Fri, Jun 21
8:15 pm - 11:29 pmHOU-ORD
27h 14m3 stops
Sun, Jun 2
8:15 pm - 7:43 pmHOU-MDW
23h 28m2 stops
Sun, Jun 2
10:30 am - 5:59 pmHOU-MDW
7h 29m1 stop
$298Delta
Find Deal
Fri, Oct 18
7:46 pm - 6:54 amHOU-MDW
11h 08m1 stop
6:00 am - 10:02 pmMDW-HOU
16h 02m1 stop
$139Frontier
Find Deal
Sat, Jun 1 - Tue, Jun 4
7:46 pm - 6:54 amHOU-MDW
11h 08m1 stop
10:41 pm - 11:57 amMDW-HOU
13h 16m1 stop
$140Frontier
Find Deal
Sat, Jun 1 - Thu, Jun 6
9:35 pm - 1:13 amHOU-ORD
27h 38m1 stop
6:45 pm - 10:02 pmORD-HOU
27h 17m1 stop
$142Frontier
Find Deal
Thu, May 30 - Mon, Jun 3
2:16 pm - 7:43 pmHOU-MDW
5h 27m1 stop
2:22 pm - 7:38 pmMDW-HOU
5h 16m1 stop
$337Allegiant Air
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Fri, May 31 - Mon, Jun 3
7:55 pm - 7:43 pmHOU-MDW
23h 48m2 stops
2:22 pm - 7:38 pmMDW-HOU
5h 16m1 stop
Thu, May 30 - Mon, Jun 3
6:00 am - 12:32 pmHOU-ORD
6h 32m1 stop
5:00 am - 9:44 amORD-HOU
4h 44m1 stop
$571American Airlines
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Fri, May 31 - Sun, Jun 16
10:15 am - 3:06 pmHOU-ORD
4h 51m1 stop
5:00 am - 9:45 amORD-HOU
4h 45m1 stop
$581American Airlines
Find Deal
Fri, May 31 - Tue, Jun 4
1:12 pm - 7:35 pmHOU-ORD
6h 23m1 stop
12:29 pm - 6:24 pmORD-HOU
5h 55m1 stop
$632Delta
Find Deal
Fri, May 31 - Tue, Jun 4
1:12 pm - 5:58 pmHOU-MDW
4h 46m1 stop
8:45 am - 3:14 pmMDW-HOU
6h 29m1 stop
$667Delta
Find Deal
Fri, May 31 - Tue, Jun 4
7:55 pm - 11:38 amHOU-ORD
15h 43m1 stop
5:05 am - 6:57 pmORD-HOU
13h 52m2 stops
Thu, May 30 - Fri, Jun 7
2:00 pm - 10:28 amHouston Tornado Bus Station-
Chicago California Ave
20h 28mnonstop
1:30 pm - 12:30 pmChicago California Ave-
Houston Tornado Bus Station
23h 00mnonstop
$470Tornado Bus
Find Deal
Thu, Sep 19 - Mon, Sep 23
1:30 pm - 10:28 amHouston Tornado Bus Station - Lockwood-
Chicago California Ave
20h 58mnonstop
1:30 pm - 12:55 pmChicago California Ave-
Houston Tornado Bus Station - Lockwood
23h 25mnonstop
$470Tornado Bus
Find Deal
Thu, Sep 19 - Mon, Sep 23
2:00 pm - 10:40 amHouston Tornado Bus Station-
Chicago California Ave
20h 40mnonstop
1:30 pm - 12:30 pmChicago California Ave-
Houston Tornado Bus Station
23h 00mnonstop
$480Tornado Bus
Find Deal
Fri, Sep 13 - Sun, Sep 15
1:30 pm - 10:40 amHouston Tornado Bus Station - Lockwood-
Chicago California Ave
21h 10mnonstop
1:30 pm - 12:55 pmChicago California Ave-
Houston Tornado Bus Station - Lockwood
23h 25mnonstop
$480Tornado Bus
Find Deal
Fri, Sep 13 - Sun, Sep 15
2:00 pm - 12:55 pmHouston Tornado Bus Station-
Milwaukee S Cesar Chavez
22h 55mnonstop
10:00 am - 12:30 pmMilwaukee S Cesar Chavez-
Houston Tornado Bus Station
26h 30mnonstop
$490Tornado Bus
Find Deal
Wed, Jun 26 - Wed, Jul 3
1:30 pm - 10:40 amHouston Tornado Bus Station - Lockwood-
Chicago California Ave
21h 10mnonstop
1:30 pm - 12:55 pmChicago California Ave-
Houston Tornado Bus Station - Lockwood
23h 25mnonstop
$500Tornado Bus
Find Deal
Sat, Jun 8 - Sat, Jun 15
1:30 pm - 10:28 amHouston Tornado Bus Station - Lockwood-
Chicago California Ave
20h 58mnonstop
1:30 pm - 12:55 pmChicago California Ave-
Houston Tornado Bus Station - Lockwood
23h 25mnonstop
$500Tornado Bus
Find Deal
Thu, Jul 4 - Mon, Jul 8
1:30 pm - 10:28 amHouston Tornado Bus Station - Lockwood-
Chicago California Ave
20h 58mnonstop
1:30 pm - 12:55 pmChicago California Ave-
Houston Tornado Bus Station - Lockwood
23h 25mnonstop
$500Tornado Bus
Find Deal
Thu, Jul 4 - Sun, Jul 7
2:00 pm - 10:40 amHouston Tornado Bus Station-
Chicago California Ave
20h 40mnonstop
1:30 pm - 12:30 pmChicago California Ave-
Houston Tornado Bus Station
23h 00mnonstop
$500Tornado Bus
Find Deal
Wed, Jun 19 - Sat, Jun 22
1:30 pm - 10:28 amHouston Tornado Bus Station - Lockwood-
Chicago California Ave
20h 58mnonstop
1:30 pm - 12:55 pmChicago California Ave-
Houston Tornado Bus Station - Lockwood
23h 25mnonstop
$500Tornado Bus
Find Deal
Wed, Jul 3 - Sun, Jul 7

Flights from Hobby to Chicago - Travel Insights & Trends

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

What is the cheapest Houston Hobby Airport to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for one-way flights from Houston Hobby Airport to Chicago.
Our data shows that the cheapest route for a one-way flight from Houston Hobby Airport to Chicago cost $302 and was between Houston Hobby Airport and Chicago Midway Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $750.

What’s the cheapest day of the week to fly from Houston Hobby Airport to Chicago?

The average price of all flights from Houston Hobby Airport to Chicago clicked on KAYAK for each day over the last 12 months.
If your flying dates are flexible, you should consider flying to Chicago on a Tuesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Houston Hobby Airport to Chicago. For your return ticket, we recommend flying on a Tuesday and avoiding Sundays for the best deals.

What is the cheapest month to fly from Houston Hobby Airport to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Houston Hobby Airport to Chicago, 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 Houston Hobby Airport to Chicago is April, where tickets cost $158 on average. On the other hand, the most expensive months are March and December, where the average cost of tickets is $266 and $264 respectively.

How far in advance should I book a flight from Houston Hobby Airport to Chicago?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Houston Hobby Airport to Chicago, 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 Houston Hobby Airport to Chicago, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 62 days before departure.

Which airlines provide the cheapest flights from Houston Hobby Airport to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the cheapest one-way ticket from Houston Hobby Airport to Chicago found on KAYAK was with Frontier for $70. Frontier proposed a round-trip connection from $140 and American Airlines from $268.

Which airlines fly non-stop between Houston Hobby Airport and Chicago?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Houston Hobby Airport to Chicago.
There is just one airline that flies from Houston Hobby Airport to Chicago direct and that is Southwest. The best one-way deal found from Southwest for the route is $291.

How many flights are there between Houston Hobby Airport and Chicago per day?

Each day, there are between 4 and 6 nonstop flights that take off from Houston Hobby Airport and land in Chicago, with an average flight time of 2h 30m. The most common departure time is 6:00 pm and most flights take off in the evening, while the most flights land at Chicago Midway Airport. Each week, there are 39 flights. The most frequent day of departure is Monday, when 15% of all weekly flights depart. The fewest flights depart on a Saturday.

Which cabin class options are there for flights between Houston Hobby Airport and Chicago?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

What’s the earliest departure time from Houston Hobby Airport to Chicago?

Early birds can take the earliest flight from Houston Hobby Airport at 5:45 am and will be landing in Chicago at 8:10 am.

What’s the latest departure time from Houston Hobby Airport to Chicago?

If you prefer to fly at night, the latest flight from Houston Hobby Airport to Chicago jets off at 10:05 pm and lands at 12:30 am.

Good to know

Low season

January

High season

May

Cheapest flight

$70
Best time to beat the crowds but there is an average 9% increase in price.
Most popular time to fly and prices are also 14% lower on average.
Flight from Houston Hobby Airport to Chicago O'Hare Airport

When to book flights from Hobby to Chicago

Are your dates flexible? Find out the best times to travel from Hobby to Chicago 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 Houston Hobby Airport to Chicago flights

  • Do Chicago airports have accommodation?

    Travelers can relax and unwind at some of the luxury hotels located within Midway Airport, like Residence Inn Midway Airport hotel located just 1 mile away from the terminal. You can stay at the Hilton O'Hare Airport Hotel right across T1, T2, and T3.

  • Does Houston Hobby Airport have services for passengers with limited mobility?

    Those with limited mobility can receive baggage and wheelchair assistance from Skycap Service. The airport also has wheelchair-accessible restrooms and elevators. Those with disabilities should communicate any other assistance they may require through the airline before their departure date.

  • What family-friendly facilities do Chicago airports have?

    There is a nursing room on Concourse C at Midway Airport. Most restrooms at Midway Airport have baby-changing stations. You will also find kid-friendly restaurants at the airport. There is a kids'play area in Terminal 2 of O'Hare Airport. Nursing rooms are also available at Terminals 1 to 5.

  • Does Hobby Airport have affordable parking options?

    An affordable parking lot at Hobby Airport is the Ecopark, where you can leave your car for a fee of around $9. Another option is the Terminal Parking garage, which charges around $13 for the daily parking option. Valet parking is also available for around $28 per day.

  • What is the cheapest flight from Houston Hobby Airport to Chicago?

    In the last 3 days, the lowest price for a flight from Houston Hobby Airport to Chicago was $70 for a one-way ticket and $140 for a round-trip.

  • Do I need a passport to fly between Houston Hobby Airport and Chicago?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airports will I be using when flying from Houston Hobby Airport to Chicago?

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

  • Which aircraft models fly most regularly from Houston Hobby Airport to Chicago?

    The Boeing 737-700 Passenger/BBJ1 (winglets) is the aircraft model that flies most regularly on the Houston Hobby Airport to Chicago flight route.

  • On which days can I fly direct from Houston Hobby Airport to Chicago?

    There are nonstop flights from Houston Hobby Airport to Chicago on a daily basis.

  • Which is the best airline for flights from Houston to Chicago, American Airlines or Frontier?

    The two airlines most popular with KAYAK users for flights from Houston to Chicago are American Airlines and Frontier. With an average price for the route of $261 and an overall rating of 7.3, American Airlines is the most popular choice. Frontier is also a great choice for the route, with an average price of $139 and an overall rating of 6.2.

  • How does KAYAK find such low prices on flights from Houston Hobby Airport to Chicago?

    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 Houston Hobby Airport to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Houston Hobby Airport 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 Houston Hobby Airport to Chicago?

    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 Chicago with an airline and back to Houston Hobby Airport with another airline.

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

    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 Chicago from Houston Hobby Airport 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 Houston to Chicago

  • If you intend to fly from Houston's Hobby Airport (HOU) to Chicago's Midway Airport (MDW) without having layovers during the trip, you can get a flight operated by Southwest Airlines. If you do not mind a layover, you can use Delta Air Lines.
  • If you’re looking for a convenient transportation means from Downtown Houston to Hobby Airport, you should book the airport shuttles, which charge a minimum fare of around $19. The shuttles will drop you off outside the baggage claim. The cheaper alternative is the 73 Bellfort Metro, which charges around $1.25.
  • Several amenities at Chicago Midway Airport make traveling through the airport easier for those with limited mobility. Elevators have raised letters and braille, family assisted care restrooms, wheelchair-accessible telephone booths, and wheelchair escorts.
  • Exploring the vibrant Chicago city in a rental car will not only be convenient but will give you maximum flexibility. Midway Airport has several car rentals, like Enterprise, located on Level 2 of the airport's parking garage. The Avis desk is located on Level 3.
  • If you have plenty of time to kill before your flight, you can explore some of Hobby Airport's famous attractions, like the museum located at the airport's terminal, or marvel at the art deco design, which reflects Houston's Aviation era.
  • If you fly in from Houston, landing at Chicago Midway Airport provides more convenience than landing at the bustling O'Hare Airport (ORD). Because Midway is relatively smaller, you can expect shorter lines and faster service. Midway Airport is also closer to Downtown Chicago than O'Hare Airport.
  • From Chicago O'Hare Airport, you can board the Blue Line L train, which takes around 45min to reach Downtown Chicago. You can find the L Train, which charges a minimum rate of approximately $5 at either Terminal 1, Terminal 2, or Terminal 3.
See more tips

Prefer to fly non-stop from Houston Hobby Airport to Chicago?

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

Nonstop departures

Houston Hobby to Chicago

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Nonstop returns

Chicago to Houston Hobby

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights
See more direct flights

Top 4 airlines serving from Hobby to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Houston to Chicago. 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 Hobby to Chicago? 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.
7.4
United AirlinesOverall score based on 10799 reviews
7.2Comfort
6.7Food
7.7Boarding
8.1Crew
7.1Entertainment
Airline reviews

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

8.0 ExcellentMichelle, Apr 2024MBS - ORD
Read more about United Airlines reviews

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The flight was delayed by 4 hours !!!!! It was very uncomfortable , and they told us only one our before departure

Left from gate 30 minutes before flight. Never been late to a flight ever. It says 15 minutes before explicitly on the ticket.

The CX617 from HK to BKK was delayed more than 1.5 hours.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

Had to board plan 2x due to lack of security check after 1st boarding

Miserable. The crew was rude, the flight was delayed 5 hours for mechanical reasons and then “weather” even though other planes were leaving.

They kept Changing the flight times. It was delayed several times and at one point it was supposed to depart at 3.40am! At which point we ended up staying overnight and booked long a separate United flight for early morning departure. The spirit flight then got moved up and left at 1.30 in the morning when it was supposed to leave at 9.40pm the night before.

Flight was delayed...not horribly late. Just before push back engine shut down for a quick replacement item that took about five minutes. After that, everything was smooth and the pilot was able to make up time in the air so that our arrival time was not too far off the original anticipated arrival time.

Only inflight purchases for food and water. Nothing comes with ticket price. Have to purchase bags, food...

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

My experience with frontier staff at the Denver airport was absolutely horrible. The manager on duty was even worst if was the worst experience I have ever had, I have never been treated so poorly as a customer in my life! The staff was extremely rude, eye rolls and attitude and then refusal to help me at all. I wish I could never fly frontier again that’s how horrible it was!

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Well I mean u get what u pay for so 🤷‍♂️

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

Book cheap flights from Houston to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Houston to Chicago found on KAYAK in the last 72 hours.
6/3Mon
1 stopFrontier
7h 16mHOU-ORD
$70
6/10Mon
1 stopFrontier
11h 49mHOU-ORD
$76
6/13Thu
1 stopFrontier
14h 57mHOU-ORD
$77
7/28Sun
1 stopSun Country Air
25h 29mHOU-ORD
$125
6/22Sat
1 stopAmerican Airlines
5h 14mHOU-ORD
$134
7/1Mon
1 stopDelta
4h 38mHOU-MDW
$199
6/21Fri
1 stopAmerican Airlines
4h 55mHOU-ORD
$216
6/2Sun
3 stops
27h 14mHOU-ORD
$247
6/2Sun
2 stops
23h 28mHOU-MDW
$254
10/18Fri
1 stopDelta
7h 29mHOU-MDW
$298

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Last minute flights from Hobby to Chicago

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 Houston to Chicago that are departing in the next 10 days.
6/1Sat
multi-stopFrontier
11h 08mHOU-MDW
6/4Tue
multi-stopFrontier
16h 02mMDW-HOU
$139
6/1Sat
multi-stopFrontier
11h 08mHOU-MDW
6/6Thu
multi-stopFrontier
13h 16mMDW-HOU
$140
5/30Thu
multi-stopFrontier
27h 38mHOU-ORD
6/3Mon
multi-stopFrontier
27h 17mORD-HOU
$142
5/31Fri
multi-stopAllegiant Air
5h 27mHOU-MDW
6/3Mon
multi-stopAllegiant Air
5h 16mMDW-HOU
$337
5/30Thu
multi-stop
23h 48mHOU-MDW
6/3Mon
multi-stop
5h 16mMDW-HOU
$558
5/31Fri
multi-stopAmerican Airlines
6h 32mHOU-ORD
6/16Sun
multi-stopAmerican Airlines
4h 44mORD-HOU
$571
5/31Fri
multi-stopAmerican Airlines
4h 51mHOU-ORD
6/4Tue
multi-stopAmerican Airlines
4h 45mORD-HOU
$581
5/31Fri
multi-stopDelta
6h 23mHOU-ORD
6/4Tue
multi-stopDelta
5h 55mORD-HOU
$632
5/31Fri
multi-stopDelta
4h 46mHOU-MDW
6/4Tue
multi-stopDelta
6h 29mMDW-HOU
$667
5/30Thu
multi-stop
15h 43mHOU-ORD
6/7Fri
multi-stop
13h 52mORD-HOU
$752

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Houston Hobby Airport - Chicago Flights

Departure:

Houston Hobby Airport (HOU)United States

Return flight deals:

Chicago - Houston Hobby Airport

Cabin classes:

$750

Compare transportation modes for Houston Hobby Airport to Chicago

Average priceAverage duration
Flights4h 41m
Buses$49420h 36m