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

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Cheap Flights from JAN to MDW starting at $128 One Way, $309 Round Trip

Prices starting at $309 for return flights and $128 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, Feb 9 - Wed, Feb 10
JAN
Jackson
MDW
Chicago
$309 Roundtrip, found 6 days ago
$309
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Feb 9 from Jackson to Chicago, returning Wed, Feb 10, priced at $309 found 6 days ago
Mon, Jan 25 - Fri, Jan 29
JAN
Jackson
MDW
Chicago
$310 Roundtrip, found 2 days ago
$310
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Mon, Jan 25 from Jackson to Chicago, returning Fri, Jan 29, priced at $310 found 2 days ago
Mon, Jan 25 - Fri, Jan 29
JAN
Jackson
MDW
Chicago
$316 Roundtrip, found 2 days ago
$316
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Mon, Jan 25 from Jackson to Chicago, returning Fri, Jan 29, priced at $316 found 2 days ago
Thu, Oct 22 - Wed, Oct 28
JAN
Jackson
MDW
Chicago
$326 Roundtrip, found 3 days ago
$326
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Oct 22 from Jackson to Chicago, returning Wed, Oct 28, priced at $326 found 3 days ago
Thu, Oct 22 - Wed, Oct 28
JAN
Jackson
MDW
Chicago
$332 Roundtrip, found 3 days ago
$332
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Oct 22 from Jackson to Chicago, returning Wed, Oct 28, priced at $332 found 3 days ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
7353 S Cicero Avenue Chicago IL
$162 nightly
The price is $188 total per night from Sep 27 to Sep 28
$188 total
Sep 27 - Sep 28
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 and ...
8/10 Very Good! (1,001 reviews)
"Na"

Reviewed on Sep 16, 2026

Holiday Inn Chicago – Midway Airport S by IHG
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$164 nightly
The price is $195 total per night from Sep 27 to Sep 28
$195 total
Sep 27 - Sep 28
Total with taxes and fees
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! (10,264 reviews)
"Clean room, funky smell tho. Super nice staff. Very helpful"

Reviewed on Sep 17, 2026

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
$248 nightly
The price is $295 total per night from Sep 25 to Sep 26
$295 total
Sep 25 - Sep 26
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 ...
Hilton Chicago
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

River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$175 nightly
The price is $208 total per night from Sep 20 to Sep 21
$208 total
Sep 20 - Sep 21
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (5,432 reviews)
"Location is great."

Reviewed on Sep 17, 2026

River Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
$179 nightly
The price is $213 total per night from Oct 13 to Oct 14
$213 total
Oct 13 - Oct 14
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very Good! (2,249 reviews)
"The room was clean and the bed comfortable but the place is worn and needs some updates. Bedside lamp did not work on right side. Door kept sticking. Water pressure was great but the shower curtain had no magnet or suction to keep it in place. Free coffee was so so. Great location. And both Angela ..."

Reviewed on Sep 17, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$164 nightly
The price is $195 total per night from Sep 27 to Sep 28
$195 total
Sep 27 - Sep 28
Total with taxes and fees
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! (10,264 reviews)
"Clean room, funky smell tho. Super nice staff. Very helpful"

Reviewed on Sep 17, 2026

Congress Plaza Hotel
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
$53 nightly
The price is $60 total per night from Oct 4 to Oct 5
$60 total
Oct 4 - Oct 5
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 ...
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
$100 nightly
The price is $110 total per night from Oct 18 to Oct 19
$110 total
Oct 18 - Oct 19
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 ...
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
$101 nightly
The price is $116 total per night from Oct 4 to Oct 5
$116 total
Oct 4 - Oct 5
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 ...
7.8/10 Good! (3,176 reviews)
"Great staff"

Reviewed on Sep 16, 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
$195 nightly
The price is $232 total per night from Sep 27 to Sep 28
$232 total
Sep 27 - Sep 28
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! (3,383 reviews)
"."

Reviewed on Sep 17, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$154 nightly
The price is $183 total per night from Sep 27 to Sep 28
$183 total
Sep 27 - Sep 28
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 ...
7.8/10 Good! (2,836 reviews)
"Hotel located in a great area that you can walk to many places or access public transportation easily. For an older building, it is well kept and clean and friendly staff. Only thing is the room was a bit basic with no refrigerator & microwave but those are accessible on the 12th floor."

Reviewed on Sep 17, 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
$53 nightly
The price is $60 total per night from Oct 4 to Oct 5
$60 total
Oct 4 - Oct 5
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 ...
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
$253 nightly
The price is $301 total per night from Sep 27 to Sep 28
$301 total
Sep 27 - Sep 28
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 ...
8.4/10 Very Good! (3,015 reviews)
"Great spot."

Reviewed on Sep 17, 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
$306 nightly
The price is $364 total per night from Sep 27 to Sep 28
$364 total
Sep 27 - Sep 28
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 ...
8.6/10 Excellent! (2,651 reviews)
"Nice hotel, good food Except the room, very dusty and hair everywhere even in sheets."

Reviewed on Sep 16, 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
$211 nightly
The price is $250 total per night from Sep 20 to Sep 21
$250 total
Sep 20 - Sep 21
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 ...
8.6/10 Excellent! (6,006 reviews)
"Excelente hotel ubicación y personal !"

Reviewed on Sep 17, 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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