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

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Cheap Flights from JAN to MDW starting at $152 One Way, $303 Round Trip

Prices starting at $303 for return flights and $152 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, Oct 28 - Sat, Oct 31
JAN
Jackson
MDW
Chicago
$303 Roundtrip, found 5 days ago
$303
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Oct 28 from Jackson to Chicago, returning Sat, Oct 31, priced at $303 found 5 days ago
Wed, Oct 28 - Sat, Oct 31
JAN
Jackson
MDW
Chicago
$308 Roundtrip, found 5 days ago
$308
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Oct 28 from Jackson to Chicago, returning Sat, Oct 31, priced at $308 found 5 days ago
Thu, Aug 20 - Mon, Aug 24
JAN
Jackson
MDW
Chicago
$310 Roundtrip, found 5 days ago
$310
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Aug 20 from Jackson to Chicago, returning Mon, Aug 24, priced at $310 found 5 days ago
Wed, Oct 28 - Sat, Oct 31
JAN
Jackson
MDW
Chicago
$313 Roundtrip, found 5 days ago
$313
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Oct 28 from Jackson to Chicago, returning Sat, Oct 31, priced at $313 found 5 days ago
Thu, Aug 20 - Mon, Aug 24
JAN
Jackson
MDW
Chicago
$315 Roundtrip, found 5 days ago
$315
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Aug 20 from Jackson to Chicago, returning Mon, Aug 24, priced at $315 found 5 days 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
$237 nightly
The price is $281 total per night from Aug 9 to Aug 10
$281 total
Aug 9 - Aug 10
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! (1,216 reviews)
"Pool wasn't working. Bathroom was moldy along the edges. The rest was great. Food was good."

Reviewed on Jul 20, 2026

Hyatt Regency McCormick Place Chicago
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
$157 nightly
The price is $187 total per night from Aug 9 to Aug 10
$187 total
Aug 9 - Aug 10
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,087 reviews)
"Close to everything."

Reviewed on Jul 20, 2026

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
$192 nightly
The price is $228 total per night from Aug 20 to Aug 21
$228 total
Aug 20 - Aug 21
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! (2,402 reviews)
"Great location . Staff very friendly"

Reviewed on Jul 20, 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

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
$189 nightly
The price is $215 total per night from Aug 6 to Aug 7
$215 total
Aug 6 - Aug 7
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! (2,864 reviews)
"clean room; excellent service"

Reviewed on Jul 20, 2026

Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
$172 nightly
The price is $204 total per night from Aug 3 to Aug 4
$204 total
Aug 3 - Aug 4
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 ...
8.2/10 Very Good! (1,799 reviews)
"Subject: Immediate Assistance Requested – Reservation Not Honored To Whom It May Concern, My family and I have arrived at your hotel with a confirmed reservation, but we have been informed by the front desk that there are no rooms available. We made this reservation in advance and expected our room ..."

Reviewed on Jul 20, 2026

The Chicago Hotel Collection Ambassador Gold Coast
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
$254 nightly
The price is $302 total per night from Aug 9 to Aug 10
$302 total
Aug 9 - Aug 10
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (1,938 reviews)
"This hotel was awful! The location was nice but the hotel is run down and is overdue for an update. The entire stay we had to use dirty towels because they kept saying they didn’t have any clean towels, as the linen company hadn’t delivered any. Full refund immediately!"

Reviewed on Jul 20, 2026

The Wade
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 Aug 10 to Aug 11
$73 total
Aug 10 - Aug 11
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! (1,987 reviews)
"The only thing I don't like is that in the room is no refrigerator."

Reviewed on Jul 20, 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
$121 nightly
The price is $134 total per night from Aug 11 to Aug 12
$134 total
Aug 11 - Aug 12
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! (1,594 reviews)
"The room want very clean but it’s convenient to park fir the week of vacation"

Reviewed on Jul 20, 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
$108 nightly
The price is $124 total per night from Aug 9 to Aug 10
$124 total
Aug 9 - Aug 10
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! (3,075 reviews)
"Clean room, shared place and breakfast place. Hotel staff were very helpful with all my needs. Overall had a stress free enjoy full stay. My flight plans ended up being cancelled so being able to get a room that night was fantastic."

Reviewed on Jul 20, 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
$144 nightly
The price is $171 total per night from Aug 10 to Aug 11
$171 total
Aug 10 - Aug 11
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! (3,204 reviews)
"That's the hotel doors were stuck always had to push them open. Half the time the key cards did not work. the room was smaller than expected and tight. bathroom was tight as well there's no extra other than the light switch in the room and a TV.there's no coffee pot there's no microwave there's no ..."

Reviewed on Jul 20, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$157 nightly
The price is $186 total per night from Aug 19 to Aug 20
$186 total
Aug 19 - Aug 20
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 ...
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 Aug 10 to Aug 11
$73 total
Aug 10 - Aug 11
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! (1,987 reviews)
"The only thing I don't like is that in the room is no refrigerator."

Reviewed on Jul 20, 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 $233 total per night from Aug 9 to Aug 10
$233 total
per night
Aug 9 - Aug 10
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! (2,920 reviews)
"This hotel offers a great breakfast and is in an excellent location. My only complaint was the check-in process, which took about 10 minutes and felt slower than at most other hotels. Additionally, one of the elevators was out of service during my visit, making the lobby area quite chaotic."

Reviewed on Jul 20, 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 $287 total per night from Aug 9 to Aug 10
$287 total
per night
Aug 9 - Aug 10
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 ...
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 $250 total per night from Aug 16 to Aug 17
$250 total
per night
Aug 16 - Aug 17
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! (6,016 reviews)
"Staff was very friendly and helpful. The hotel is in a great location and the rooms were clean. Our room was adjacent to the parking garage and possibly where the dumpsters are located because it got pretty loud in the middle of the night. Other than that the hotel was great!"

Reviewed on Jul 20, 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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