JAN - CHI

$139 Find Cheap Flights from Jackson 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 Jackson to Chicago departing on 4/8. 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.
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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Jackson 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 Jackson to Chicago, as well as popular online travel agencies
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Cheap Flight Deals from Jackson to Chicago (JAN-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Jackson to Chicago that are departing in the next months. 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 Jackson to Chicago

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Jackson to Chicago.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
3:36 pm - 9:15 pmJAN-ORD
5h 39m1 stop
3:59 pm - 9:48 pmORD-JAN
5h 49m1 stop
$277American Airlines
Find Deal
Wed, Apr 16 - Wed, Apr 23
12:11 pm - 4:14 pmJAN-MDW
4h 03m1 stop
6:00 am - 11:22 amMDW-JAN
5h 22m1 stop
$277Delta
Find Deal
Tue, Mar 25 - Thu, Apr 10
3:20 pm - 8:10 pmJAN-MDW
4h 50m1 stop
9:10 am - 2:30 pmMDW-JAN
5h 20m1 stop
$297Southwest
Find Deal
Fri, Mar 21 - Wed, Mar 26
7:00 am - 2:24 pmJAN-ORD
7h 24m1 stop
5:36 pm - 11:50 pmORD-JAN
6h 14m1 stop
$297American Airlines
Find Deal
Tue, Mar 18 - Sat, Mar 22
3:20 pm - 8:10 pmJAN-MDW
4h 50m1 stop
6:10 am - 2:30 pmMDW-JAN
8h 20m2 stops
$302Southwest
Find Deal
Fri, Mar 21 - Wed, Mar 26
3:20 pm - 11:15 pmJAN-MDW
7h 55m2 stops
6:10 am - 2:30 pmMDW-JAN
8h 20m2 stops
$307Southwest
Find Deal
Fri, Mar 21 - Wed, Mar 26
1:07 pm - 5:42 pmJAN-MDW
4h 35m1 stop
6:00 am - 10:19 amMDW-JAN
4h 19m1 stop
$312Delta
Find Deal
Thu, May 8 - Sun, May 11
7:20 am - 1:13 pmJAN-ORD
5h 53m1 stop
5:00 am - 10:28 amORD-JAN
5h 28m1 stop
$312American Airlines
Find Deal
Thu, May 8 - Sun, May 11
2:07 pm - 9:30 pmJAN-ORD
7h 23m1 stop
6:00 am - 11:29 amORD-JAN
5h 29m1 stop
$331United Airlines
Find Deal
Sat, May 31 - Wed, Jun 4
7:00 am - 12:13 pmJAN-ORD
5h 13m1 stop
9:50 pm - 11:19 amORD-JAN
13h 29m1 stop
$415United Airlines
Find Deal
Tue, Mar 25 - Thu, Apr 10

Flights from Jackson to Chicago - Travel Insights & Trends

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

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

The average price of all round-trip flights from Jackson 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 Saturday, 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 Jackson to Chicago. For your return ticket, we recommend flying on a Wednesday and avoiding Sundays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Jackson 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 Jackson to Chicago is April, where tickets cost $381 (return) on average. On the other hand, the most expensive months are January and August, where the average cost of round-trip tickets is $581 and $496 respectively.

Good to know

Low season

February

High season

September

Cheapest flight

$139
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Jackson to Chicago O'Hare Airport

When to book flights from Jackson to Chicago

Are your dates flexible? Find out the best times to travel from Jackson 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 flights from Jackson to Chicago

  • What is the cheapest flight from Jackson to Chicago?

    In the last 3 days, the lowest price for a flight from Jackson to Chicago was $139 for a one-way ticket and $277 for a round-trip.

  • Do I need a passport to fly between Jackson 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 Jackson to Chicago?

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

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

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Jackson to Chicago?

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

  • Which is the best airline for flights from Jackson to Chicago, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Jackson to Chicago are Southwest and Delta. With an average price for the route of $392 and an overall rating of 8.1, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $513 and an overall rating of 8.0.

  • How does KAYAK find such low prices on flights from Jackson 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 Jackson to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Jackson 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 Jackson 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 Jackson with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Jackson 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 Jackson up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 3 airlines serving from Jackson to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Jackson 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 Jackson 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.
8.1
SouthwestOverall score based on 4333 reviews
7.6Entertainment
8.7Crew
8.2Boarding
8.1Comfort
7.1Food
Airline reviews

WiFi on the flight was not working. Thus, entertainment options were limited.

8.0 ExcellentJames, Feb 2025SRQ - DEN
Read more Southwest reviews

WiFi on the flight was not working. Thus, entertainment options were limited.

Great flight staff. Ease of boarding. Overall, very uneventful and easy trip.

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

Gate agents were informative and friendly… flight attendants were as well. Had a fun time chatting about their legacy AirTran experiences as a former fan of the airline that Southwest acquired.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Wi Fi was horrible kept cutting out the whole time and too expensive

I really like open seating. I hate that I've heard this is going away. This is one of the unique things that makes Southwest my goto choice.

Boarding was a little late, but made up for it. It was quick to taxi to the runway, since it's a smallish airport.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

Multiple delays and gate changes. Arrived at final destination 6 hours late. All rental cars had been taken.

Delta is a premier airline so my expectations are most always met.

Seats are much much more comfortable than United, which is what I usually fly

Zero updates from the pilots for 30 minutes in the tarmac

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

I loved having a most black flight crew during Black History Month; rather by design or accident I appreciated the representation. ❤️

This was the second flight this week with flight attendant Marcus I’m not sure if his last name is Lane or Lang but this guy is awesome. He funny, attentive and his service is 5 stars. Marcus makes business travel more enjoyable !

Although the flight left late, we arrived early. It was one of the quickest boarding and off boarding experiences I’ve had. It was kind of annoying the only drinks they had were water, coffee, and tea. The flight was very smooth, temperature was just right, and flight attendants were friendly.

Lower number on this flight so spaced out passengers. Able to enjoy more room to relax during flight. It was lovely.

Kind staff. Snacks are small but that’s the new normal.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

It was nice being on a flight that had working wifi. The boarding was quick - why don’t all airlines have small boarding groups window to aisle? Makes so much sense!!! I was disappointed to be the first person stopped to have to gate check my carryon. Especially when there was plenty of overhead space at the back! But I get it…keeps it moving. Crew was nice.

The flight from Buffalo to Chicago was on an older and smaller plane. Seating was tight. Looking closely at the interior of the aircraft there were definitely signs of aging and wear.

The flight encountered a delay exceeding 4 hours. The food voucher issued was valued at $12, insufficient to cover our meal expenses. Consequently, I was unable to take my medication, leading to a drop in blood sugar levels and exacerbating my anxiety.

Everything you need to know for your flight from Jackson to Chicago

Information on your arrival and departure airports

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