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

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Cheap Flights from JAN to MDW starting at $122 One Way, $242 Round Trip

Prices starting at $242 for return flights and $122 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, Nov 11 - Tue, Nov 18
JAN
Jackson
MDW
Chicago
$242 Roundtrip, found 5 days ago
$242
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Nov 11 from Jackson to Chicago, returning Tue, Nov 18, priced at $242 found 5 days ago
Thu, Nov 27 - Tue, Dec 9
JAN
Jackson
MDW
Chicago
$257 Roundtrip, found 1 day ago
$257
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Nov 27 from Jackson to Chicago, returning Tue, Dec 9, priced at $257 found 1 day ago
Wed, Oct 29 - Fri, Oct 31
JAN
Jackson
MDW
Chicago
$258 Roundtrip, found 6 days ago
$258
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Oct 29 from Jackson to Chicago, returning Fri, Oct 31, priced at $258 found 6 days ago
Mon, Nov 10 - Tue, Nov 18
JAN
Jackson
MDW
Chicago
$259 Roundtrip, found 5 days ago
$259
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Nov 10 from Jackson to Chicago, returning Tue, Nov 18, priced at $259 found 5 days ago
Tue, Oct 28 - Fri, Oct 31
JAN
Jackson
MDW
Chicago
$262 Roundtrip, found 6 days ago
$262
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Oct 28 from Jackson to Chicago, returning Fri, Oct 31, priced at $262 found 6 days ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street, Chicago, IL
$171 nightly
The price is $201 total per night from Oct 5 to Oct 6
$201 total
Oct 5 - Oct 6
Total with taxes and fees
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,022 reviews)
"Excellent staff, very helpful and welcoming."

Reviewed on Sep 24, 2025

Holiday Inn & Suites Chicago - Downtown by IHG
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
$150 nightly
The price is $176 total per night from Oct 19 to Oct 20
$176 total
Oct 19 - Oct 20
Total with taxes and fees
Stay at this 3.5-star 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! (1,558 reviews)
"clean"

Reviewed on Oct 1, 2025

Crowne Plaza Chicago West Loop by IHG
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
$145 nightly
The price is $170 total per night from Nov 2 to Nov 3
$170 total
Nov 2 - Nov 3
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (9,370 reviews)
"Very Clean Hotel, me and my friend enjoyed our stay here. It is an older hotel but the room was really nice"

Reviewed on Sep 30, 2025

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.

Hotels In Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
$145 nightly
The price is $170 total per night from Nov 2 to Nov 3
$170 total
Nov 2 - Nov 3
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (9,370 reviews)
"Very Clean Hotel, me and my friend enjoyed our stay here. It is an older hotel but the room was really nice"

Reviewed on Sep 30, 2025

Congress Plaza 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
$192 nightly
The price is $226 total per night from Nov 2 to Nov 3
$226 total
Nov 2 - Nov 3
Total with taxes and fees
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.4/10 Very Good! (5,023 reviews)
"Clean , a great location and the amenities are awesome"

Reviewed on Oct 1, 2025

Embassy Suites by Hilton Chicago Downtown River North
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
$150 nightly
The price is $176 total per night from Nov 2 to Nov 3
$176 total
Nov 2 - Nov 3
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! (2,999 reviews)
"Outstanding stay! Would stay again."

Reviewed on Oct 1, 2025

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
$52 nightly
The price is $59 total per night from Oct 26 to Oct 27
$59 total
Oct 26 - Oct 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! (1,647 reviews)
"Motel 6 Elk Grove village O’hare very nice , Clean rooms, all the stuff super nice, and you can get premium rooms w fridge, coffee maker and all prices very low!!! Come and see yourself"

Reviewed on Sep 24, 2025

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 Oct 5 to Oct 6
$101 total
Oct 5 - Oct 6
Total with taxes and fees
Stay at this 3-star golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
7/10 Good! (1,099 reviews)
"Clean"

Reviewed on Oct 1, 2025

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
$85 nightly
The price is $97 total per night from Nov 2 to Nov 3
$97 total
Nov 2 - Nov 3
Total with taxes and fees
Stay at this 3-star 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! (2,655 reviews)
"None"

Reviewed on Oct 1, 2025

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
$139 nightly
The price is $163 total per night from Oct 27 to Oct 28
$163 total
Oct 27 - Oct 28
Total with taxes and fees
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
7.8/10 Good! (2,422 reviews)
"I stayed in a shared quad with females, The room wasn’t bad for the price they do however need to install more lighting in the rooms because there was only one light working in the room plus the one in the bathroom so the room was very dark. The staff are great!!! They were super helpful answered ..."

Reviewed on Oct 2, 2025

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL
$118 nightly
The price is $139 total per night from Nov 2 to Nov 3
$139 total
Nov 2 - Nov 3
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 ...
7.2/10 Good! (2,385 reviews)
"Great location and close to train. Helpful staff"

Reviewed on Sep 28, 2025

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
$52 nightly
The price is $59 total per night from Oct 26 to Oct 27
$59 total
Oct 26 - Oct 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! (1,647 reviews)
"Motel 6 Elk Grove village O’hare very nice , Clean rooms, all the stuff super nice, and you can get premium rooms w fridge, coffee maker and all prices very low!!! Come and see yourself"

Reviewed on Sep 24, 2025

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
$213 nightly
The price is $250 total per night from Nov 2 to Nov 3
$250 total
Nov 2 - Nov 3
Total with taxes and fees
Stay at this 4-star 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! (2,750 reviews)
"The room was excellent except the conditioner bottle was broken and never fixed"

Reviewed on Oct 1, 2025

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
$215 nightly
The price is $249 total per night from Oct 23 to Oct 24
$249 total
Oct 23 - Oct 24
Total with taxes and fees
Stay at this 4-star 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! (2,000 reviews)
"I recently stayed at Palmer House, and overall, it was a decent experience. The location was convenient—close to local shops, restaurants, and public transportation—which made exploring the area easy and enjoyable. The room itself was clean and adequately furnished. Staff were polite and responsive, ..."

Reviewed on Oct 1, 2025

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
$192 nightly
The price is $226 total per night from Nov 2 to Nov 3
$226 total
Nov 2 - Nov 3
Total with taxes and fees
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.4/10 Very Good! (5,023 reviews)
"Clean , a great location and the amenities are awesome"

Reviewed on Oct 1, 2025

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.

More to Explore

More to Explore