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Chicago (MDW) to Jackson (JAN) Flights from ₹15,466

Fares on this route currently start from ₹15,466. Compare live MDW to JAN prices, non-stop and connecting flights, departure times and airline choices before booking. Use the search panel to change origin, destination, passengers, cabin and trip type instantly.
MDW → JAN Approx. 1073.42 km 14 Jul 2026 Live inventory
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Showing 25 of 131 live flights
Southwest Airlines
WN-2902
11:25
07/14/2026
MDW
Chicago Midway International Airport
9h 20m
2 Stops
⏱ STL · 3h 25mSTL Airport⏱ HOU · 1h 15mHOU Airport
20:45
07/14/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹15,466
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-5080
19:10
07/14/2026
MDW
Chicago Midway International Airport
25h 35m
1 Stop
⏱ HOU · 21h 35mHOU Airport
20:45
07/15/2026
+1
JAN
Jackson-Medgar Wiley Evers International Airport
₹15,892
per person
✕ Non-refundable🔥 Last 2 seats4 fare options
Southwest Airlines
WN-736
10:15
07/14/2026
MDW
Chicago Midway International Airport
25h 30m
1 Stop
⏱ HOU · 19h 40mHOU Airport
11:45
07/15/2026
+1
JAN
Jackson-Medgar Wiley Evers International Airport
₹16,397
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-59
18:05
07/14/2026
MDW
Chicago Midway International Airport
26h 40m
1 Stop
⏱ HOU · 21h 5mHOU Airport
20:45
07/15/2026
+1
JAN
Jackson-Medgar Wiley Evers International Airport
₹16,397
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-3869
15:10
07/14/2026
MDW
Chicago Midway International Airport
29h 35m
1 Stop
⏱ HOU · 22h 40mHOU Airport
20:45
07/15/2026
+1
JAN
Jackson-Medgar Wiley Evers International Airport
₹16,903
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-3869
15:10
07/14/2026
MDW
Chicago Midway International Airport
20h 35m
1 Stop
⏱ HOU · 13h 45mHOU Airport
11:45
07/15/2026
+1
JAN
Jackson-Medgar Wiley Evers International Airport
₹16,903
per person
✕ Non-refundable4 fare options
Delta Air Lines
DL-1285
06:00
07/14/2026
MDW
Chicago Midway International Airport
4h 0m
1 Stop
⏱ ATL · 0h 43mATL Airport
10:00
07/14/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹17,872
per person
✕ Non-refundable6 fare options
Delta Air Lines
DL-1285
06:00
07/14/2026
MDW
Chicago Midway International Airport
6h 5m
1 Stop
⏱ ATL · 2h 53mATL Airport
12:05
07/14/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹17,872
per person
✕ Non-refundable6 fare options
Delta Air Lines
DL-2426
08:03
07/14/2026
ORD
Chicago Midway International Airport
4h 2m
1 Stop
⏱ ATL · 0h 44mATL Airport
12:05
07/14/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹17,872
per person
✕ Non-refundable5 fare options
Delta Air Lines
DL-1264
05:30
07/14/2026
ORD
Chicago Midway International Airport
4h 30m
1 Stop
⏱ ATL · 1h 11mATL Airport
10:00
07/14/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹17,872
per person
✕ Non-refundable5 fare options
Delta Air Lines
DL-1247
06:35
07/14/2026
ORD
Chicago Midway International Airport
5h 30m
1 Stop
⏱ ATL · 2h 13mATL Airport
12:05
07/14/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹17,872
per person
✕ Non-refundable5 fare options
Delta Air Lines
DL-1264
05:30
07/14/2026
ORD
Chicago Midway International Airport
6h 35m
1 Stop
⏱ ATL · 3h 21mATL Airport
12:05
07/14/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹17,872
per person
✕ Non-refundable5 fare options
Southwest Airlines
WN-1702
10:10
07/14/2026
MDW
Chicago Midway International Airport
10h 35m
3 Stops
⏱ MKE · 0h 35mMKE Airport⏱ DAL · 1h 35mDAL Airport⏱ HOU · 2h 30mHOU Airport
20:45
07/14/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹18,087
per person
✕ Non-refundable🔥 Last 5 seats2 fare options
Southwest Airlines
WN-1702
10:10
07/14/2026
MDW
Chicago Midway International Airport
10h 35m
3 Stops
⏱ MKE · 0h 35mMKE Airport⏱ DAL · 2h 35mDAL Airport⏱ HOU · 1h 35mHOU Airport
20:45
07/14/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹18,087
per person
✕ Non-refundable🔥 Last 5 seats2 fare options
Southwest Airlines
WN-709
12:00
07/14/2026
MDW
Chicago Midway International Airport
8h 45m
1 Stop
⏱ HOU · 4h 45mHOU Airport
20:45
07/14/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹20,278
per person
✕ Non-refundable6 fare options
Southwest Airlines
WN-2661
05:05
07/14/2026
MDW
Chicago Midway International Airport
6h 40m
2 Stops
⏱ DAL · 1h 10mDAL Airport⏱ HOU · 0h 40mHOU Airport
11:45
07/14/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹20,425
per person
✕ Non-refundable6 fare options
Southwest Airlines
WN-2733
11:50
07/14/2026
MDW
Chicago Midway International Airport
8h 55m
2 Stops
⏱ BNA · 1h 20mBNA Airport⏱ HOU · 2h 45mHOU Airport
20:45
07/14/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹20,425
per person
✕ Non-refundable4 fare options
Southwest Airlines
WN-3869
15:10
07/14/2026
MDW
Chicago Midway International Airport
3h 35m
1 Stop
⏱ BNA · 0h 45mBNA Airport
18:45
07/14/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹20,699
per person
✕ Non-refundable14 fare options
Southwest Airlines
WN-4497
07:10
07/14/2026
MDW
Chicago Midway International Airport
4h 35m
1 Stop
⏱ HOU · 0h 40mHOU Airport
11:45
07/14/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹20,699
per person
✕ Non-refundable14 fare options
Southwest Airlines
WN-736
10:15
07/14/2026
MDW
Chicago Midway International Airport
10h 30m
1 Stop
⏱ HOU · 4h 35mHOU Airport
20:45
07/14/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹20,784
per person
✕ Non-refundable8 fare options
Southwest Airlines
WN-2733
11:50
07/14/2026
MDW
Chicago Midway International Airport
6h 55m
1 Stop
⏱ BNA · 4h 10mBNA Airport
18:45
07/14/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹21,233
per person
✕ Non-refundable14 fare options
Southwest Airlines
WN-3572
12:05
07/14/2026
MDW
Chicago Midway International Airport
6h 40m
2 Stops
⏱ MCI · 1h 0mMCI Airport⏱ BNA · 1h 20mBNA Airport
18:45
07/14/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹21,379
per person
✕ Non-refundable6 fare options
Southwest Airlines
WN-2902
11:25
07/14/2026
MDW
Chicago Midway International Airport
7h 20m
2 Stops
⏱ STL · 2h 35mSTL Airport⏱ BNA · 1h 5mBNA Airport
18:45
07/14/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹21,379
per person
✕ Non-refundable6 fare options
Southwest Airlines
WN-2902
11:25
07/14/2026
MDW
Chicago Midway International Airport
7h 20m
2 Stops
⏱ STL · 1h 10mSTL Airport⏱ BNA · 2h 30mBNA Airport
18:45
07/14/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹21,379
per person
✕ Non-refundable6 fare options
Southwest Airlines
WN-2665
11:25
07/14/2026
MDW
Chicago Midway International Airport
7h 20m
2 Stops
⏱ RDU · 1h 55mRDU Airport⏱ BNA · 0h 40mBNA Airport
18:45
07/14/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹21,379
per person
✕ Non-refundable4 fare options
😕 No flights match your filters.
Chicago (MDW)
📍 Chicago Midway International Airport
🌍 United States
🕐 GMT -6
📐 Latitude: 41.785999
📐 Longitude: -87.752403
Jackson (JAN)
📍 Jackson-Medgar Wiley Evers International Airport
🌍 United States
🕐 GMT -6
📐 Latitude: 32.3111991882
📐 Longitude: -90.0758972168

✈ Distance: Chicago,USA to Jackson,USA — 1073.42 km

📅 Results on this page are loaded for 14 Jul 2026. Click Load more flights to expand the full list on this page.

Chicago to Jackson — what to expect when booking

The MDW–JAN route is served by multiple carriers throughout the year. Fares on this route can move quickly — a price available now may not be there 30 minutes later.

If your dates are flexible, try shifting your departure by a day or two using the date strip above. Mid-week departures often show lower base fares compared to weekend starts on many routes.

The distance between Chicago,USA and Jackson,USA is approximately 1073.42 km.

Before you book

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More flights from Chicago (MDW)
63 routes
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More flights from Jackson (JAN)
8 routes
Jackson → Atlanta
JAN → ATL
Jackson → Charlotte
JAN → CLT
Jackson → Chicago
JAN → ORD
Jackson → Fort Worth
JAN → DFW
Jackson → Houston
JAN → IAH
Jackson → Houston
JAN → HOU
Jackson → Orlando
JAN → MCO
Jackson → Washington DC
JAN → DCA
❓ Frequently asked questions — Chicago to Jackson flights

Generally yes — fares on most routes are most competitive around 4–6 weeks before departure. Booking earlier usually means better availability and a lower base fare when your dates are fixed.

The straight-line distance between Chicago,USA (MDW) and Jackson,USA (JAN) is approximately 1073.42 km. Actual flying distance may vary slightly depending on routing.

Non-stop availability on this route varies by airline schedule and season. Use the filters below to quickly check whether direct options are available on your selected date.

Mid-week departures often show lower prices than weekend travel on many routes. Use the date strip above to compare nearby days quickly.