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

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Cheap Flights from JAN to MDW starting at $129 One Way, $351 Round Trip

Prices starting at $351 for return flights and $129 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.

Fri, Mar 13 - Mon, Mar 16
JAN
Jackson
MDW
Chicago
$351 Roundtrip, found 1 day ago
$351
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, Mar 13 from Jackson to Chicago, returning Mon, Mar 16, priced at $351 found 1 day ago
Fri, Mar 13 - Mon, Mar 16
JAN
Jackson
MDW
Chicago
$361 Roundtrip, found 1 day ago
$361
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, Mar 13 from Jackson to Chicago, returning Mon, Mar 16, priced at $361 found 1 day ago
Wed, Mar 25 - Fri, Mar 27
JAN
Jackson
MDW
Chicago
$371 Roundtrip, found 3 hours ago
$371
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Wed, Mar 25 from Jackson to Chicago, returning Fri, Mar 27, priced at $371 found 3 hours ago
Fri, Aug 28 - Sun, Aug 30
JAN
Jackson
MDW
Chicago
$374 Roundtrip, found 6 days ago
$374
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Fri, Aug 28 from Jackson to Chicago, returning Sun, Aug 30, priced at $374 found 6 days ago
Wed, Mar 25 - Fri, Mar 27
JAN
Jackson
MDW
Chicago
$377 Roundtrip, found 3 hours ago
$377
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Wed, Mar 25 from Jackson to Chicago, returning Fri, Mar 27, priced at $377 found 3 hours ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
710 S Seeley Avenue Chicago IL
$109 nightly
The price is $128 total per night from Jan 15 to Jan 16
$128 total
Jan 15 - Jan 16
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Popular attractions United Center and Chicago ...
9.6/10 Exceptional! (415 reviews)
Great room, great staff that was very professional! Everything was outstanding!

Reviewed on Jan 6, 2026

Hampton Inn & Suites Chicago Medical District UIC
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
$164 nightly
The price is $192 total per night from Jan 19 to Jan 20
$192 total
Jan 19 - Jan 20
Total with taxes and fees
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (2,507 reviews)
Clean, good breakfast, quiet. Easy acces

Reviewed on Jan 9, 2026

Hilton Chicago
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
$91 nightly
The price is $107 total per night from Jan 18 to Jan 19
$107 total
Jan 18 - Jan 19
Total with taxes and fees
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 ...
8.8/10 Excellent! (1,851 reviews)
Everything was good. Staff was very friendly.

Reviewed on Jan 6, 2026

Crowne Plaza Chicago West Loop by IHG
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

Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
$164 nightly
The price is $192 total per night from Jan 19 to Jan 20
$192 total
Jan 19 - Jan 20
Total with taxes and fees
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (2,507 reviews)
Clean, good breakfast, quiet. Easy acces

Reviewed on Jan 9, 2026

Hilton Chicago
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
$168 nightly
The price is $192 total per night from Jan 18 to Jan 19
$192 total
Jan 18 - Jan 19
Total with taxes and fees
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 ...
8.4/10 Very Good! (2,231 reviews)
This stay was perfection from beginning to end. Totally wonderful experience in every way.

Reviewed on Jan 9, 2026

Palmer House a Hilton Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
$89 nightly
The price is $105 total per night from Jan 18 to Jan 19
$105 total
Jan 18 - Jan 19
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (3,688 reviews)
Very satisfying

Reviewed on Jan 11, 2026

Hilton Chicago/Magnificent Mile Suites
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
$37 nightly
The price is $41 total per night from Jan 26 to Jan 27
$41 total
Jan 26 - Jan 27
Total with taxes and fees
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! (1,758 reviews)
Room was perfect

Reviewed on Jan 6, 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
$91 nightly
The price is $101 total per night from Jan 12 to Jan 13
$101 total
Jan 12 - Jan 13
Total with taxes and fees
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 ...
7.2/10 Good! (1,247 reviews)
The room was okay. It needs updates, but it works for an overnight stay. The shuttle was on time and courteous.

Reviewed on Jan 5, 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
$61 nightly
The price is $69 total per night from Jan 15 to Jan 16
$69 total
Jan 15 - Jan 16
Total with taxes and fees
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! (2,775 reviews)
Yes

Reviewed on Jan 7, 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
$66 nightly
The price is $78 total per night from Feb 2 to Feb 3
$78 total
Feb 2 - Feb 3
Total with taxes and fees
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. ...
7.8/10 Good! (2,698 reviews)
Clean. Everyone very accommodating. Great location. Safe

Reviewed on Jan 7, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$72 nightly
The price is $85 total per night from Jan 12 to Jan 13
$85 total
Jan 12 - Jan 13
Total with taxes and fees
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! (2,503 reviews)
Check in person was great. View of train tracks was not great and was noisy Location very convenient location to university

Reviewed on Jan 5, 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
$37 nightly
The price is $41 total per night from Jan 26 to Jan 27
$41 total
Jan 26 - Jan 27
Total with taxes and fees
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! (1,758 reviews)
Room was perfect

Reviewed on Jan 6, 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
$121 nightly
The price is $142 total per night from Jan 21 to Jan 22
$142 total
Jan 21 - Jan 22
Total with taxes and fees
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! (2,772 reviews)
Just very crowded. 15 minute wait for a drink. Even longer line in the morning for a fresh omelette. We did stay over a holiday.

Reviewed on Jan 7, 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
$168 nightly
The price is $192 total per night from Jan 18 to Jan 19
$192 total
Jan 18 - Jan 19
Total with taxes and fees
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 ...
8.4/10 Very Good! (2,231 reviews)
This stay was perfection from beginning to end. Totally wonderful experience in every way.

Reviewed on Jan 9, 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
$93 nightly
The price is $110 total per night from Jan 19 to Jan 20
$110 total
Jan 19 - Jan 20
Total with taxes and fees
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 ...
8.4/10 Very Good! (5,531 reviews)
All good

Reviewed on Jan 9, 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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