Cheap flights from JAN to MDW (Evers Intl. to Midway Intl.)

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Cheap Flights from JAN to MDW starting at $149 One Way, $277 Round Trip

Prices starting at $277 for return flights and $149 for one-way flights to Midway Intl. were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Apr 21 - Tue, May 5
JAN
Jackson
MDW
Chicago
$277 Roundtrip, found 20 hours ago
$277
Roundtrip
found 20 hours ago
Select Delta flight, departing Tue, Apr 21 from Jackson to Chicago, returning Tue, May 5, priced at $277 found 20 hours ago
Sat, Apr 25 - Tue, May 5
JAN
Jackson
MDW
Chicago
$290 Roundtrip, found 20 hours ago
$290
Roundtrip
found 20 hours ago
Select Delta flight, departing Sat, Apr 25 from Jackson to Chicago, returning Tue, May 5, priced at $290 found 20 hours ago
Mon, Apr 20 - Tue, May 5
JAN
Jackson
MDW
Chicago
$293 Roundtrip, found 20 hours ago
$293
Roundtrip
found 20 hours ago
Select Delta flight, departing Mon, Apr 20 from Jackson to Chicago, returning Tue, May 5, priced at $293 found 20 hours ago
Mon, Mar 30 - Tue, Apr 14
JAN
Jackson
MDW
Chicago
$306 Roundtrip, found 20 hours ago
$306
Roundtrip
found 20 hours ago
Select Delta flight, departing Mon, Mar 30 from Jackson to Chicago, returning Tue, Apr 14, priced at $306 found 20 hours ago
Sat, Apr 25 - Mon, May 4
JAN
Jackson
MDW
Chicago
$307 Roundtrip, found 20 hours ago
$307
Roundtrip
found 20 hours ago
Select Delta flight, departing Sat, Apr 25 from Jackson to Chicago, returning Mon, May 4, priced at $307 found 20 hours ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is $109 total per night from Feb 27 to Feb 28
$109 total
per night
Feb 27 - Feb 28
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (9,888 reviews)
Kind staff and a nice view of the city, close to a ton of things in the area!

Reviewed on Feb 26, 2026

Congress Plaza Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street Chicago IL
The price is $131 total per night from Mar 1 to Mar 2
$131 total
per night
Mar 1 - Mar 2
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
9/10 Wonderful! (1,995 reviews)
Bathroom wasn’t clean and hair on towels

Reviewed on Feb 25, 2026

Crowne Plaza Chicago West Loop by IHG
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
55 E 11th Street Chicago IL
The price is $112 total per night from Mar 1 to Mar 2
$112 total
per night
Mar 1 - Mar 2
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
8.8/10 Excellent! (1,868 reviews)
I had an extremely great stay. Staff was amazing. I never got her name but the young lady that was doing check ins on Saturday morning was extremely sweet.

Reviewed on Feb 25, 2026

Hilton Garden Inn Chicago Downtown South Loop
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels In Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is $109 total per night from Feb 27 to Feb 28
$109 total
per night
Feb 27 - Feb 28
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (9,888 reviews)
Kind staff and a nice view of the city, close to a ton of things in the area!

Reviewed on Feb 26, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
The price is $179 total per night from Mar 4 to Mar 5
$179 total
per night
Mar 4 - Mar 5
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
9.4/10 Exceptional! (3,416 reviews)
Loved the hotel and ambiance. My stay was truly amazing. I just wish they would’ve had an ice machine and microwaves inside the hotel . It would’ve been 5 stars if they had microwaves and ice. Also the receptionist attitude wasn’t the best. I didn’t feel very welcomed and seemed like she was just ...

Reviewed on Feb 26, 2026

Hotel Riu Plaza Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
The price is $120 total per night from Mar 4 to Mar 5
$120 total
per night
Mar 4 - Mar 5
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.6/10 Excellent! (5,685 reviews)
Service was great, and the staff was very kind.

Reviewed on Feb 26, 2026

Embassy Suites by Hilton Chicago Downtown River North
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Chicago Hotels With Airport Transportation

Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave Elk Grove Village IL
The price is $48 total per night from Mar 22 to Mar 23
$48 total
per night
Mar 22 - Mar 23
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,848 reviews)
My stay was relaxing. The staff was helpful and welcoming. I'm glad I stayed here. The rooms were clean and quiet. I checked in with Tiffany. She was very kind and made me feel valued as a guest. Thank You!!

Reviewed on Feb 22, 2026

Motel 6 Elk Grove Village, IL - O'Hare
Country Inn & Suites by Radisson, Chicago O'Hare South, IL

Country Inn & Suites by Radisson, Chicago O'Hare South, IL

3 out of 5
777 E Grand Avenue Bensenville IL
The price is $101 total per night from Feb 28 to Mar 1
$101 total
per night
Feb 28 - Mar 1
Book a stay at this golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
7.4/10 Good! (1,287 reviews)
Everything was good. My baby enjoyed her birthday stay. Only bad part was me I let my croc shoes please put them up I'm coming to get them

Reviewed on Feb 26, 2026

Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Comfort Suites Chicago O'Hare Airport

Comfort Suites Chicago O'Hare Airport

3 out of 5
4200 North River Road Schiller Park IL
The price is $90 total per night from Mar 1 to Mar 2
$90 total
per night
Mar 1 - Mar 2
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and ...
8/10 Very Good! (2,923 reviews)
The room had a leaky tub spout and ripped couch.

Reviewed on Feb 25, 2026

Comfort Suites Chicago O'Hare Airport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Low Priced Chicago Hotels

Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
The price is $96 total per night from Mar 2 to Mar 3
$96 total
per night
Mar 2 - Mar 3
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (2,780 reviews)
Great bar areas! Very clean rooms

Reviewed on Feb 26, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
The price is $112 total per night from Mar 5 to Mar 6
$112 total
per night
Mar 5 - Mar 6
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
7.4/10 Good! (2,521 reviews)
🎯

Reviewed on Feb 25, 2026

Travelodge by Wyndham Downtown Chicago
Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave Elk Grove Village IL
The price is $48 total per night from Mar 22 to Mar 23
$48 total
per night
Mar 22 - Mar 23
Stay at this motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,848 reviews)
My stay was relaxing. The staff was helpful and welcoming. I'm glad I stayed here. The rooms were clean and quiet. I checked in with Tiffany. She was very kind and made me feel valued as a guest. Thank You!!

Reviewed on Feb 22, 2026

Motel 6 Elk Grove Village, IL - O'Hare
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Chicago

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4 out of 5
511 North Columbus Drive Chicago IL
The price is $146 total per night from Mar 5 to Mar 6
$146 total
per night
Mar 5 - Mar 6
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (2,809 reviews)
Customer service was great. There’s a great team working the front desk. Room was clean and held enough space for 4 adults and one child. Beds were really comfortable and slept great. Enjoyed the refreshments when we had time as well. Highly recommend staying there for a future visit.

Reviewed on Feb 26, 2026

Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
The price is $202 total per night from Mar 6 to Mar 7
$202 total
per night
Mar 6 - Mar 7
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.6/10 Excellent! (2,318 reviews)
Beautiful hotel with exceptional service.

Reviewed on Feb 25, 2026

Palmer House a Hilton Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
The price is $120 total per night from Mar 4 to Mar 5
$120 total
per night
Mar 4 - Mar 5
Stay at this hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular ...
8.6/10 Excellent! (5,685 reviews)
Service was great, and the staff was very kind.

Reviewed on Feb 26, 2026

Embassy Suites by Hilton Chicago Downtown River North
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

JAN to MDW Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date
JAN Address & GPS
Address:
100 International Drive, Suite 300
Jackson MS, 39296-8109
United States
IATA Code:
JAN
Longitude:
-90.074955
Latitude:
32.309896
Time Zone:
America/Chicago
MDW Address & GPS
Address:
5700 South Cicero
Chicago IL, 60638
United States
IATA Code:
MDW
Longitude:
-87.740871
Latitude:
41.788136
Time Zone:
America/Chicago

Frequently asked questions

Are there non-stop flights from Jackson Municipal Airport to Chicago Airport?
Nonstop flights aren't an option when it comes to getting from Evers Intl. Airport (JAN) to Chicago Airport. However, there are plenty of companies that service this route with just a single stopover, including Southwest Airlines, Delta Air Lines and United Airlines.
What is the shortest flight from Jackson Municipal Airport to Chicago Airport?
The shortest flight time from Jackson to Chicago is around 3 hours and 39 minutes. Order your favorite tipple from the drink cart, go over your travel itinerary or get to know your neighbors — you'll have enough time on this medium-haul trip.
How many hours flight from JAN to Midway Intl. Airport (MDW)?
Get comfortable, because the average plane trip from JAN to Midway Airport is 3 hours and 44 minutes. Listen to a few podcasts, stick your nose in a book ... You'll have enough time to relax and unwind.
What airlines have the most flights from Evers Intl. Airport (JAN) to Chicago Airport?
There are no airlines operating direct flights between Evers Intl. Airport (JAN) and Chicago Airport. Plan ahead and reserve a multi-stop or one-stop plane ticket.

Map To Nearby Hotels

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.

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