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Showing 25
of 121
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18:06
05/11/2026
ORD
Chicago Midway International Airport
5h 12m
1 Stop
⏱ ATL · 1h 34m ATL Airport
23:18
05/11/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹14,751
per person
Select →
✕ Non-refundable
07:07
05/11/2026
ORD
Chicago Midway International Airport
5h 36m
1 Stop
⏱ ATL · 2h 8m ATL Airport
12:43
05/11/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹14,751
per person
Select →
✕ Non-refundable
05:30
05/11/2026
ORD
Chicago Midway International Airport
7h 13m
1 Stop
⏱ ATL · 3h 50m ATL Airport
12:43
05/11/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹14,751
per person
Select →
✕ Non-refundable
17:10
05/11/2026
MDW
Chicago Midway International Airport
6h 8m
1 Stop
⏱ ATL · 2h 40m ATL Airport
23:18
05/11/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹14,751
per person
Select →
✕ Non-refundable 2 fare options
06:23
05/11/2026
MDW
Chicago Midway International Airport
6h 20m
1 Stop
⏱ ATL · 2h 59m ATL Airport
12:43
05/11/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹14,751
per person
Select →
✕ Non-refundable 2 fare options
Southwest Airlines
WN-455
06:55
05/11/2026
MDW
Chicago Midway International Airport
4h 45m
1 Stop
⏱ HOU · 0h 45m HOU Airport
11:40
05/11/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹19,589
per person
Select →
✕ Non-refundable 🔥 Last 1 seats 10 fare options
Southwest Airlines
WN-3964
12:10
05/11/2026
MDW
Chicago Midway International Airport
8h 50m
1 Stop
⏱ HOU · 4h 50m HOU Airport
21:00
05/11/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹20,119
per person
Select →
✕ Non-refundable 🔥 Last 2 seats 4 fare options
Southwest Airlines
WN-3329
11:50
05/11/2026
MDW
Chicago Midway International Airport
9h 10m
2 Stops
⏱ OMA · 2h 55m OMA Airport ⏱ HOU · 1h 5m HOU Airport
21:00
05/11/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹20,267
per person
Select →
✕ Non-refundable 🔥 Last 2 seats 4 fare options
Southwest Airlines
WN-3233
12:00
05/11/2026
MDW
Chicago Midway International Airport
7h 5m
1 Stop
⏱ BNA · 4h 10m BNA Airport
19:05
05/11/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹21,065
per person
Select →
✕ Non-refundable 🔥 Last 3 seats 10 fare options
Southwest Airlines
WN-3404
11:40
05/11/2026
MDW
Chicago Midway International Airport
9h 20m
2 Stops
⏱ DEN · 1h 40m DEN Airport ⏱ HOU · 1h 5m HOU Airport
21:00
05/11/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹21,213
per person
Select →
✕ Non-refundable 4 fare options
08:10
05/11/2026
ORD
Chicago Midway International Airport
4h 33m
1 Stop
⏱ ATL · 1h 18m ATL Airport
12:43
05/11/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹21,367
per person
Select →
✕ Non-refundable
Southwest Airlines
WN-658
14:40
05/11/2026
ORD
Chicago Midway International Airport
4h 25m
1 Stop
⏱ BNA · 1h 20m BNA Airport
19:05
05/11/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹21,679
per person
Select →
✕ Non-refundable 🔥 Last 1 seats 9 fare options
Southwest Airlines
WN-3225
10:25
05/11/2026
MDW
Chicago Midway International Airport
10h 35m
2 Stops
⏱ AUS · 4h 25m AUS Airport ⏱ HOU · 1h 5m HOU Airport
21:00
05/11/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹21,742
per person
Select →
✕ Non-refundable 🔥 Last 2 seats 4 fare options
American Airlines
AA-1109
18:41
05/11/2026
ORD
Chicago Midway International Airport
5h 18m
1 Stop
⏱ CLT · 0h 55m CLT Airport
23:59
05/11/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹23,136
per person
Select →
✕ Non-refundable 9 fare options
American Airlines
AA-2946
16:17
05/11/2026
ORD
Chicago Midway International Airport
7h 42m
1 Stop
⏱ CLT · 3h 18m CLT Airport
23:59
05/11/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹23,136
per person
Select →
✕ Non-refundable 9 fare options
Southwest Airlines
WN-2149
09:25
05/11/2026
MDW
Chicago Midway International Airport
26h 55m
1 Stop
⏱ HOU · 20h 40m HOU Airport
12:20
05/12/2026
+1
JAN
Jackson-Medgar Wiley Evers International Airport
₹23,890
per person
Select →
✕ Non-refundable 5 fare options
Southwest Airlines
WN-2950
11:55
05/11/2026
MDW
Chicago Midway International Airport
7h 10m
2 Stops
⏱ MCI · 0h 45m MCI Airport ⏱ BNA · 1h 55m BNA Airport
19:05
05/11/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹24,052
per person
Select →
✕ Non-refundable 🔥 Last 2 seats 9 fare options
Southwest Airlines
WN-1422
11:40
05/11/2026
MDW
Chicago Midway International Airport
7h 25m
2 Stops
⏱ STL · 1h 15m STL Airport ⏱ BNA · 2h 20m BNA Airport
19:05
05/11/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹24,052
per person
Select →
✕ Non-refundable 4 fare options
Southwest Airlines
WN-155
11:40
05/11/2026
MDW
Chicago Midway International Airport
9h 20m
2 Stops
⏱ ABQ · 1h 50m ABQ Airport ⏱ HOU · 1h 0m HOU Airport
21:00
05/11/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹24,052
per person
Select →
✕ Non-refundable 🔥 Last 4 seats 4 fare options
Southwest Airlines
WN-3548
10:00
05/11/2026
MDW
Chicago Midway International Airport
9h 5m
2 Stops
⏱ MCI · 2h 40m MCI Airport ⏱ BNA · 1h 55m BNA Airport
19:05
05/11/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹24,052
per person
Select →
✕ Non-refundable 🔥 Last 1 seats 4 fare options
06:05
05/11/2026
ORD
Chicago Midway International Airport
4h 58m
1 Stop
⏱ DFW · 0h 42m DFW Airport
11:03
05/11/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹24,071
per person
Select →
✕ Non-refundable 9 fare options
Southwest Airlines
WN-3225
10:25
05/11/2026
MDW
Chicago Midway International Airport
10h 35m
2 Stops
⏱ MAF · 0h 50m MAF Airport ⏱ HOU · 2h 20m HOU Airport
21:00
05/11/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹24,553
per person
Select →
✕ Non-refundable 🔥 Last 4 seats 4 fare options
Southwest Airlines
WN-3964
12:10
05/11/2026
MDW
Chicago Midway International Airport
24h 10m
1 Stop
⏱ HOU · 20h 10m HOU Airport
12:20
05/12/2026
+1
JAN
Jackson-Medgar Wiley Evers International Airport
₹24,808
per person
Select →
✕ Non-refundable 5 fare options
14:59
05/11/2026
ORD
Chicago Midway International Airport
5h 39m
1 Stop
⏱ ATL · 2h 15m ATL Airport
20:38
05/11/2026
JAN
Jackson-Medgar Wiley Evers International Airport
₹24,909
per person
Select →
✕ Non-refundable
Southwest Airlines
WN-2959
21:35
05/11/2026
MDW
Chicago Midway International Airport
19h 55m
1 Stop
⏱ BNA · 17h 5m BNA Airport
17:30
05/12/2026
+1
JAN
Jackson-Medgar Wiley Evers International Airport
₹25,020
per person
Select →
✕ Non-refundable 5 fare options
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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 11 May 2026 . Click View all flights for the complete live search.
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
Compare nearby dates The date strip above lets you scan nearby fares without restarting the search.
Open full search for more control Route page shows a limited live set. Full search opens the complete inventory with fresh results.
Check fare details Each result shows baggage, refundability and fare details before you proceed.
More flights from Chicago (MDW)
68 routes
More flights from Jackson (JAN)
8 routes
❓ Frequently asked questions — Chicago to Jackson flights
▼ Is it worth booking Chicago to Jackson flights in advance?
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.
▼ How far is Chicago from Jackson by air?
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.
▼ Are there non-stop flights from MDW to JAN?
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.
▼ What is the cheapest day to fly from Chicago to Jackson?
Mid-week departures often show lower prices than weekend travel on many routes. Use the date strip above to compare nearby days quickly.