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

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Cheap Flights from JAN to MDW starting at $157 One Way, $303 Round Trip

Prices starting at $303 for return flights and $157 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 6 days ago
$303
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Oct 28 from Jackson to Chicago, returning Sat, Oct 31, priced at $303 found 6 days ago
Wed, Oct 28 - Sat, Oct 31
JAN
Jackson
MDW
Chicago
$308 Roundtrip, found 6 days ago
$308
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Oct 28 from Jackson to Chicago, returning Sat, Oct 31, priced at $308 found 6 days ago
Thu, Aug 20 - Mon, Aug 24
JAN
Jackson
MDW
Chicago
$310 Roundtrip, found 6 days ago
$310
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Aug 20 from Jackson to Chicago, returning Mon, Aug 24, priced at $310 found 6 days ago
Wed, Oct 28 - Sat, Oct 31
JAN
Jackson
MDW
Chicago
$313 Roundtrip, found 6 days ago
$313
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Oct 28 from Jackson to Chicago, returning Sat, Oct 31, priced at $313 found 6 days ago
Thu, Aug 20 - Mon, Aug 24
JAN
Jackson
MDW
Chicago
$315 Roundtrip, found 6 days ago
$315
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Aug 20 from Jackson to Chicago, returning Mon, Aug 24, priced at $315 found 6 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 10 to Aug 11
$281 total
Aug 10 - Aug 11
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! (1,220 reviews)
"The front desk staff were professional and friendly."

Reviewed on Jul 21, 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 ...
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
$184 nightly
The price is $219 total per night from Aug 20 to Aug 21
$219 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! (2,404 reviews)
"Other than a computer glitch the stay was flawless. This is my third time at this property. The rooms are well proportioned, top class bathrooms and of course clean. Convenient restaurant on property and many options close by."

Reviewed on Jul 21, 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 ...
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 Jul 26 to Jul 27
$204 total
Jul 26 - Jul 27
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 ...
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! (1,932 reviews)
"There wasn’t any Clean linen available upon request. Sheets / Towels etc. The Breakfast Menu/ Bar was great."

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 ...
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! (1,600 reviews)
"This was a great hotel to stay at for the night. We loved the helpfulness of the staff. They picked us up at the airport EARLY in the morning and even kept trying to get a hold of me with my spotty internet. The beds felt good and the room was nicely cleaned and smelled very nice. We got a good night's ..."

Reviewed on Jul 21, 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! (3,084 reviews)
"The property was very run down and dirty. The first room we were given was supposed to accommodate 4 adults, the pull out sofa would be large enough for one adult or two small children, but not two teens or above. Also, it would not pull out fully in order to be slept on, the mattress was about 2 ..."

Reviewed on Jul 21, 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
$142 nightly
The price is $169 total per night from Aug 10 to Aug 11
$169 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! (3,205 reviews)
"We booked with freehand Chicago despite the reviews because the New York location was awesome. We called the day before check in to see if we could get a mini fridge in our room because I needed to store breast milk. We were told they are typically all in use during the weekend and they couldn’t ..."

Reviewed on Jul 21, 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 Aug 10 to Aug 11
$183 total
Aug 10 - Aug 11
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 ...
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
$218 nightly
The price is $259 total per night from Aug 9 to Aug 10
$259 total
Aug 9 - Aug 10
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 ...
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
$249 nightly
The price is $297 total per night from Aug 9 to Aug 10
$297 total
Aug 9 - Aug 10
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! (2,535 reviews)
"The staff was the best"

Reviewed on Jul 21, 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
$203 nightly
The price is $242 total per night from Aug 9 to Aug 10
$242 total
Aug 9 - Aug 10
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! (5,990 reviews)
"Great location. Big rooms. Nice staff. No water pressure in washrooms. Washrooms could use some TLC and a tub reglazing"

Reviewed on Jul 21, 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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