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

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Cheap Flights from JAN to MDW starting at $172 One Way, $359 Round Trip

Prices starting at $359 for return flights and $172 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.

Wed, Aug 12 - Sat, Aug 15
JAN
Jackson
MDW
Chicago
$359 Roundtrip, found 1 day ago
$359
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Aug 12 from Jackson to Chicago, returning Sat, Aug 15, priced at $359 found 1 day ago
Wed, Aug 12 - Sat, Aug 15
JAN
Jackson
MDW
Chicago
$359 Roundtrip, found 1 day ago
$359
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Aug 12 from Jackson to Chicago, returning Sat, Aug 15, priced at $359 found 1 day ago
Fri, Aug 21 - Wed, Aug 26
JAN
Jackson
MDW
Chicago
$363 Roundtrip, found 1 day ago
$363
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Aug 21 from Jackson to Chicago, returning Wed, Aug 26, priced at $363 found 1 day ago
Wed, Aug 12 - Sat, Aug 15
JAN
Jackson
MDW
Chicago
$364 Roundtrip, found 1 day ago
$364
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Aug 12 from Jackson to Chicago, returning Sat, Aug 15, priced at $364 found 1 day ago
Wed, Aug 12 - Sat, Aug 15
JAN
Jackson
MDW
Chicago
$368 Roundtrip, found 1 day ago
$368
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Aug 12 from Jackson to Chicago, returning Sat, Aug 15, priced at $368 found 1 day ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
$203 nightly
The price is $241 total per night from Jul 2 to Jul 3
$241 total
Jul 2 - Jul 3
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,095 reviews)
"Still-attractive hotel despite being the older of the two hotels next to McCormick Place with excellent beds, adequate space, good facilities. It is a very good choice next to the convention centre given its location and cleanliness. The staff were very helpful."

Reviewed on Jun 2, 2026

Hyatt Regency McCormick Place 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
$153 nightly
The price is $182 total per night from Jul 6 to Jul 7
$182 total
Jul 6 - Jul 7
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 ...
9/10 Wonderful! (2,238 reviews)
"I had an amazing time in Chicago, not one complaint. Everyone was pleasant and my room was clean."

Reviewed on Jun 4, 2026

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 $173 total per night from Jun 29 to Jun 30
$173 total
Jun 29 - Jun 30
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! (10,171 reviews)
"Good spot. Nice staff. Great location."

Reviewed on Jun 5, 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.

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 $173 total per night from Jun 29 to Jun 30
$173 total
Jun 29 - Jun 30
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! (10,171 reviews)
"Good spot. Nice staff. Great location."

Reviewed on Jun 5, 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
$154 nightly
The price is $183 total per night from Jun 28 to Jun 29
$183 total
Jun 28 - Jun 29
Total with taxes and fees
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,518 reviews)
"Clean room"

Reviewed on Jun 3, 2026

The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
$135 nightly
The price is $154 total per night from Jun 28 to Jun 29
$154 total
Jun 28 - Jun 29
Total with taxes and fees
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,616 reviews)
"The property was well maintained, and the location was excellent. Kim and Liz provided outstanding customer service throughout my stay—they were professional, welcoming, and truly made a positive impact. They deserve recognition for their exceptional work. Unfortunately, my experience at the Red ..."

Reviewed on Jun 4, 2026

Hyatt Regency O'Hare 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.

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
$65 nightly
The price is $73 total per night from Jun 25 to Jun 26
$73 total
Jun 25 - Jun 26
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! (1,949 reviews)
"For a simple stay, this place fits the bill. The staff was awesome. The area doesn’t have much but a Subway Sandwich shop that’s open til 11pm on Sundays, which was a plus for me, so plan on renting a car or grabbing a ride share for all of your activities."

Reviewed on Jun 3, 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
$102 nightly
The price is $113 total per night from Jun 28 to Jun 29
$113 total
Jun 28 - Jun 29
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 ...
7.6/10 Good! (1,476 reviews)
"not as well maintained as i'd like--felt a bit like staying in an old motel 6 in the 1980s"

Reviewed on Jun 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
$94 nightly
The price is $108 total per night from Jun 8 to Jun 9
$108 total
Jun 8 - Jun 9
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! (3,029 reviews)
"The bus shuttle operator was rude and wasn't accurate i was taken Schaumburg when I wanted to go to Schiller park"

Reviewed on Jun 4, 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
$137 nightly
The price is $162 total per night from Jul 6 to Jul 7
$162 total
Jul 6 - Jul 7
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. ...
8/10 Very Good! (3,057 reviews)
"Beautifully maintained historic, but updated property. Incredible views, great walking area, full of just about anything! Great trip!"

Reviewed on Jun 4, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$134 nightly
The price is $159 total per night from Jun 28 to Jun 29
$159 total
Jun 28 - Jun 29
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! (2,599 reviews)
"I'm asking just for hot water they cannot attend to my needs"

Reviewed on Jun 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
$65 nightly
The price is $73 total per night from Jun 25 to Jun 26
$73 total
Jun 25 - Jun 26
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! (1,949 reviews)
"For a simple stay, this place fits the bill. The staff was awesome. The area doesn’t have much but a Subway Sandwich shop that’s open til 11pm on Sundays, which was a plus for me, so plan on renting a car or grabbing a ride share for all of your activities."

Reviewed on Jun 3, 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
$239 nightly
The price is $284 total per night from Jul 6 to Jul 7
$284 total
Jul 6 - Jul 7
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! (2,868 reviews)
"Everything was good, food, staff, cleaning service. Except the Bed convertible Sofa was dirty under the cushions need some cleaning."

Reviewed on Jun 4, 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
$209 nightly
The price is $248 total per night from Jul 2 to Jul 3
$248 total
Jul 2 - Jul 3
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! (2,476 reviews)
"Check in was horrible. The longest lines you can imagine….face me 250 Hilton points….not useful for me. Property is beautiful if you look closely but it is not well maintained."

Reviewed on Jun 4, 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
$208 nightly
The price is $247 total per night from Jun 14 to Jun 15
$247 total
Jun 14 - Jun 15
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! (5,957 reviews)
"Great hotel and excellent service."

Reviewed on Jun 5, 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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