JAN - CHI

$155 Find Cheap Flights from Jackson to Chicago - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$309
Typical prices: $366-$571
Southwest
Mon 11/5Sat 11/10
JAN - MDW • 1 stop
Cheapest one-way
$155
Typical prices: $268-$388
Delta
Wed 12/5
JAN - MDW • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Jackson and Chicago. You'll need to take a connecting flight to reach the destination.
Insights
Insights
Top routes
JAN - ORD
Cheapest • 4% average savings
JAN - MDW
Most popular
Insights
Insights
When to travel
January
Cheapest • 26% price drop
August
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Houston Hobby (HOU)
Cheapest • Avg $390 (round-trip)
Atlanta Hartsfield-Jackson (ATL)
Shortest trip • 4h 51m (one-way)
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Jackson to Chicago (JAN-CHI)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Jackson to Chicago

Tue, Nov 3 - Thu, Nov 5
American Airlines Logo
7:00 am - 12:24 pmJAN  Jackson-Evers Intl-ORD Chicago O'Hare Intl
5h 24m1 stop Dallas/Fort Worth
American Airlines Logo
6:00 am - 11:45 amORD  Chicago O'Hare Intl-JAN Jackson-Evers Intl
5h 45m1 stop Dallas/Fort Worth
$309American Airlines
Tue, Oct 6 - Tue, Oct 13
American Airlines Logo
12:15 pm - 7:16 pmJAN  Jackson-Evers Intl-ORD Chicago O'Hare Intl
7h 01m1 stop Dallas/Fort Worth
American Airlines Logo
4:45 pm - 11:25 pmORD  Chicago O'Hare Intl-JAN Jackson-Evers Intl
6h 40m1 stop Charlotte Douglas
$309American Airlines
Thu, Oct 1 - Wed, Oct 7
Delta Logo
5:14 pm - 11:59 pmJAN  Jackson-Evers Intl-ORD Chicago O'Hare Intl
6h 45m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:27 am - 10:25 amORD  Chicago O'Hare Intl-JAN Jackson-Evers Intl
4h 58m1 stop Atlanta Hartsfield-Jackson
$309Delta
Tue, Nov 3 - Thu, Nov 5
Delta Logo
1:04 pm - 5:47 pmJAN  Jackson-Evers Intl-ORD Chicago O'Hare Intl
4h 43m1 stop Atlanta Hartsfield-Jackson
Delta Logo
10:35 am - 2:38 pmORD  Chicago O'Hare Intl-JAN Jackson-Evers Intl
4h 03m1 stop Atlanta Hartsfield-Jackson
$309Delta
Thu, Nov 5 - Tue, Nov 10
Southwest Logo
8:15 pm - 1:05 amJAN  Jackson-Evers Intl-MDW Chicago Midway
4h 50m1 stop Houston Hobby
Southwest Logo
12:45 pm - 5:35 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
4h 50m1 stop Nashville Intl
$309Southwest
Sat, Dec 5 - Mon, Dec 7
American Airlines Logo
5:48 pm - 12:01 amJAN  Jackson-Evers Intl-ORD Chicago O'Hare Intl
6h 13m1 stop Charlotte Douglas
American Airlines Logo
3:52 pm - 10:52 pmORD  Chicago O'Hare Intl-JAN Jackson-Evers Intl
7h 00m1 stop Dallas/Fort Worth
$309American Airlines
Wed, Oct 7 - Wed, Oct 14
Delta Logo
11:10 am - 4:58 pmJAN  Jackson-Evers Intl-ORD Chicago O'Hare Intl
5h 48m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:27 am - 12:14 pmORD  Chicago O'Hare Intl-JAN Jackson-Evers Intl
6h 47m1 stop Atlanta Hartsfield-Jackson
$309Delta
Tue, Nov 3 - Thu, Nov 5
Southwest Logo
6:15 pm - 11:05 pmJAN  Jackson-Evers Intl-MDW Chicago Midway
4h 50m1 stop Houston Hobby
Southwest Logo
12:25 pm - 10:05 pmMDW  Chicago Midway-JAN Jackson-Evers Intl
9h 40m1 stop Houston Hobby
$314Southwest
Tue, Feb 2 - Wed, Feb 3
United Airlines Logo
1:57 pm - 9:01 amJAN  Jackson-Evers Intl-ORD Chicago O'Hare Intl
19h 04m2 stops Houston George Bush Intcntl Lambert-St Louis
United Airlines Logo
7:50 pm - 11:13 amORD  Chicago O'Hare Intl-JAN Jackson-Evers Intl
15h 23m1 stop Houston George Bush Intcntl
$527United Airlines
Sat, Oct 24 - Mon, Oct 26
United Airlines Logo
7:00 am - 8:30 pmJAN  Jackson-Evers Intl-ORD Chicago O'Hare Intl
13h 30m2 stops Houston George Bush Intcntl Lambert-St Louis
United Airlines Logo
5:27 pm - 1:19 pmORD  Chicago O'Hare Intl-JAN Jackson-Evers Intl
19h 52m1 stop Houston George Bush Intcntl
$527United Airlines
Booking Insights

Price, demand and travel trends for Jackson to Chicago flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights from Jackson to Chicago with more confidence.

How much is a round-trip flight from Jackson to Chicago?

Round-trip flights from Jackson to Chicago start at $309. Prices are below average for this route right now, with typical round-trip fares ranging from $366 to $571. The lowest price found in the past 5 days was $309 on Southwest.

What is the cheapest Jackson to Chicago flight route?

There's little price difference between Jackson to Chicago routes. They average around $439 round-trip, based on KAYAK data over the past 12 months.

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

Wednesday is the cheapest day of the week to fly from Jackson to Chicago, it is 19% cheaper than the average day. Sunday is the most expensive day with flight prices 58% higher than average. Based on deals found by KAYAK users in the last 12 months.

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

  • January is the cheapest month to fly from Jackson to Chicago at $324 round-trip.
  • March ($565) and May ($521) are the most expensive months.
  • The price difference between flying in the cheapest and most expensive months is 74% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

Find deals

Key details for Jackson to Chicago flights

Low season

February

Cheapest flight

$155
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly with an average 6% increase in price.
Flight from Jackson to Chicago Midway 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

Your Jackson to Chicago flight questions, answered

Find helpful route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • Which airports can I use when flying from Jackson to Chicago?

    Flights from Jackson to Chicago usually depart from Jackson-Evers Intl (JAN) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

  • What cabin classes can I book on flights from Jackson to Chicago?

    Only Economy Class is available on flights from Jackson to Chicago.

  • Which airports do connecting flights from Jackson to Chicago pass through?

    One-stop flights from Jackson to Chicago most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 57% of one-stop connections
    • Charlotte Douglas (CLT) - 15% of one-stop connections
    • Dallas/Fort Worth (DFW) - 14% of one-stop connections
    • Nashville Intl (BNA) - 6% of one-stop connections

    Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

  • Can I save money by using flexible dates for flights from Jackson to Chicago?

    Yes. Being flexible with your travel dates can save you up to 49% on the Jackson to Chicago route. Wednesday is the cheapest departure day at $353 round-trip on average, while Sunday is the most expensive at $690, a difference of $337. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • What popular places can I visit in Chicago?

    Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago on KAYAK.

  • How long is a flight from Jackson to Chicago?

    A nonstop flight from Jackson to Chicago takes 0h 00m, covering 674 miles.

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

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

  • Have flight prices from Jackson to Chicago changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $309 to $2,207. That means the highest observed fare was about 7x higher than the lowest one.

  • How are flight prices from Jackson to Chicago looking right now?

    One-way fares from Jackson to Chicago are currently lower than usual. Average one-way flight prices are about $189, which is 47% below the typical average for this route.

  • Is it cheaper to take a train or bus instead of flying between Jackson and Chicago?

    Based on prices from the last 5 days, flying between Jackson and Chicago is around $309 round-trip, with a flight time of about 4h 50m. Recent train fares are around $261, with a trip time of about 19h 20m. Compared with flying, recent train fares are roughly 16% lower. However, taking the train takes about 14+ hours longer each way.

  • How much time can I save by choosing a different layover airport from Jackson to Chicago?

    Flying via Atlanta Hartsfield-Jackson (ATL) gives the shortest average 1-stop total travel time at 4h 51m, compared with 5h 31m via Houston Hobby (HOU) and 5h 36m via Charlotte Douglas (CLT).

  • What car rental options are available in Chicago?

    Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

    · Routes Car & Truck Rentals
    · Europcar
    · Hertz
    · Dollar
    · Ace

    Near Chicago Midway Airport (MDW) — daily rates from around $32:

    · Hertz
    · Dollar
    · Budget
    · Alamo
    · Rent-A-Wreck

    Near Chicago Greater Rockford Airport (RFD) — daily rates from around $30:

    · Alamo
    · Enterprise Rent-A-Car
    · Budget
    · Avis
    · National

  • How much should I expect to pay for a Jackson to Chicago flight?

    Round-trip flights from Jackson to Chicago range from $366 to $571, with an average of $435 over the past 12 months. Anything below $366 counts as a good deal.

Your guide to booking Jackson to Chicago flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates can be flexible, aim for a Wednesday departure instead of Sunday. On this route, Wednesday flights average $353 - about $337 less than Sunday (49% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Jackson to Chicago trip for January. Fares historically average $324 round-trip in that month - typically $241 less than the most expensive month, which is March (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.
    - DoubleTree by Hilton Chicago Midway Airport
    - Holiday Inn Chicago - Midway Airport S by IHG
    - Skylark Motel

More options for your flight from Jackson to Chicago

Complete your trip to Chicago with a hotel stay or car rental

Car rentals in Chicago
Hotels in Chicago
Vacations in Chicago