JAN - CHI

$144 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
7:30 am - 1:18 pmJAN-ORD
5h 48m1 stop
4:40 pm - 11:50 pmORD-JAN
7h 10m1 stop
$287American Airlines
Find Deal
Thu, Mar 13 - Tue, Mar 18
7:29 am - 4:14 pmJAN-ORD
8h 45m1 stop
5:36 pm - 11:53 pmORD-JAN
6h 17m1 stop
$307American Airlines
Find Deal
Thu, Feb 27 - Fri, Feb 28
12:20 pm - 9:35 pmJAN-MDW
9h 15m1 stop
8:40 am - 7:25 pmMDW-JAN
10h 45m2 stops
$312Southwest
Find Deal
Thu, Feb 27 - Fri, Feb 28
12:20 pm - 9:35 pmJAN-MDW
9h 15m2 stops
11:30 am - 7:25 pmMDW-JAN
7h 55m2 stops
$317Southwest
Find Deal
Thu, Feb 27 - Fri, Feb 28
7:29 am - 4:14 pmJAN-ORD
8h 45m1 stop
4:07 pm - 9:43 pmORD-JAN
5h 36m1 stop
$327American Airlines
Find Deal
Fri, Feb 28 - Fri, Mar 7
12:20 pm - 6:10 pmJAN-MDW
5h 50m1 stop
6:20 am - 2:45 pmMDW-JAN
8h 25m1 stop
$327Southwest
Find Deal
Fri, Feb 28 - Fri, Mar 7
1:58 pm - 9:24 pmJAN-ORD
7h 26m1 stop
7:00 am - 9:59 pmORD-JAN
14h 59m2 stops
$468United Airlines
Find Deal
Thu, Mar 13 - Tue, Mar 18
10:47 am - 4:14 pmJAN-MDW
5h 27m1 stop
6:00 am - 10:04 amMDW-JAN
4h 04m1 stop
$488Delta
Find Deal
Thu, Mar 13 - Tue, Mar 18
5:16 pm - 12:15 amJAN-ORD
6h 59m1 stop
7:55 pm - 1:23 pmORD-JAN
17h 28m1 stop
$651United Airlines
Find Deal
Thu, Feb 13 - Mon, Feb 17
10:47 am - 6:02 pmJAN-MDW
7h 15m2 stops
6:00 am - 10:04 amMDW-JAN
4h 04m1 stop
$830Delta
Find Deal
Thu, Mar 13 - Tue, Mar 18

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 $371 (return) on average. On the other hand, the most expensive months are March and January, where the average cost of round-trip tickets is $695 and $661 respectively.

Good to know

Low season

February

High season

September

Cheapest flight

$144
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 15% 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 $144 for a one-way ticket and $287 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 $505 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 4587 reviews
8.1Comfort
8.2Boarding
8.7Crew
7.1Food
7.7Entertainment
Airline reviews

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.

10.0 ExcellentAnonymous, Jan 2025ATL - LGA
Read more Southwest reviews

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.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

It was 2 hours 45 minutes late, for no apparently clear reason.

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.

Flight left early and arrived early. the whole trip was excellent.

Seats were really tight and the seat belts did not give enough slack.

I like in St George and prefer to fly out of CDC than SGU. Hopefully, they will continue the flights out of Cedar

Broken jer bridge. Poor communication about it. Lost 2 of 4 luggage pieces

Overall, it was okay. Seat was a little cramped. Would’ve liked more substantial snacks or opportunity to buy some.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

I was with one of the last zones to board. It was kind of annoying to finally get called to board and my whole section was already on the plane. Clearly they boarded with previous zones. So by the time I got on board, there were no spaces for my luggage above my head. I had to put my luggage 4+ rows behind me, which meant that I had to wait even longer to get off the plane, since I had to wait for those rows to clear the aisle before I could retrieve my luggage and exit the plane. This also held up the plane cleaners, as they couldn't service my row until I cleared it, so they were all standing there waiting for me, while I'm standing there waiting for the other passengers to clear the aisle. Anyways, I wasn't in a rush this time, so I just waited, but I could see that being a problem in the future. Now, I could have checked my luggage, of course, but coincidentally, a friend of mine on the same flight got their luggage damaged (wheel completely knocked off) and was told by the Baggage Attendant in the airport that Delta doesn't "cover wheel damage" on luggage. This was disappointing to hear. I'm glad I didn't check mine through. If it were my luggage, I'd be highly frustrated to hear that. It makes me not want to check my luggage in the future.

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

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.

Airplane was cold. Flight attendants were rude. Phone charger did not work. No food available.

3hour delay In the last 3 months i had 3 flights and 2 of these had a more than 2:40 hrs delayed

My initial flight to ORD was extended without reason. We circled the airport a few time and then drove on the ground for at least 20 minutes. These kinds of delays are annoying but somewhat expected… it would be nice if the crew would make an announcement to give updates on how long we could expect to be delayed.

The flight was uneventful. What was a problem was I was delayed getting home one entire day because the flight from Sacramento was delayed. That made getting to my connecting flight impossible. I had to stay another night at the hotel and incur that expense as a result.

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

Information on your arrival and departure airports

Compare transportation modes for Jackson to Chicago

Average priceAverage duration
Flights5h 27m
Trains$22815h 51m

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