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 4 days ago
$303
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Oct 28 from Jackson to Chicago, returning Sat, Oct 31, priced at $303 found 4 days ago
Wed, Oct 28 - Sat, Oct 31
JAN
Jackson
MDW
Chicago
$308 Roundtrip, found 4 days ago
$308
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Oct 28 from Jackson to Chicago, returning Sat, Oct 31, priced at $308 found 4 days ago
Thu, Aug 20 - Mon, Aug 24
JAN
Jackson
MDW
Chicago
$310 Roundtrip, found 4 days ago
$310
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Thu, Aug 20 from Jackson to Chicago, returning Mon, Aug 24, priced at $310 found 4 days ago
Wed, Oct 28 - Sat, Oct 31
JAN
Jackson
MDW
Chicago
$313 Roundtrip, found 4 days ago
$313
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Oct 28 from Jackson to Chicago, returning Sat, Oct 31, priced at $313 found 4 days ago
Thu, Aug 20 - Mon, Aug 24
JAN
Jackson
MDW
Chicago
$315 Roundtrip, found 4 days ago
$315
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Thu, Aug 20 from Jackson to Chicago, returning Mon, Aug 24, priced at $315 found 4 days ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Hotel Chicago West Loop, SureStay Collection by Best Western

Hotel Chicago West Loop, SureStay Collection by Best Western

2.5 out of 5
1622 W Jackson Blvd Chicago IL
$166 nightly
The price is $198 total per night from Aug 16 to Aug 17
$198 total
Aug 16 - Aug 17
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
Hotel Chicago West Loop, SureStay Collection by Best Western
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 ...
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! (1,084 reviews)
"Room size"

Reviewed on Jul 19, 2026

Holiday Inn & Suites Chicago - Downtown 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
$190 nightly
The price is $226 total per night from Aug 3 to Aug 4
$226 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! (1,781 reviews)
"Close to the town Over charged for parking even though we paid for rooms and we had to pay for parking"

Reviewed on Jul 19, 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 ...
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! (1,986 reviews)
"It's a Motel 6 so expectations shouldn't be too high but this place was pretty aweful. The room was baren. A bed, a tv and a table, not much else. The carpets in the main hallways were pretty dirty. There was a garbage can on the first floor by the ice machine that was overflowing (items on the ground) ..."

Reviewed on Jul 18, 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
$120 nightly
The price is $133 total per night from Aug 9 to Aug 10
$133 total
Aug 9 - Aug 10
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! (1,590 reviews)
"Nice shuttle, breakfast, staff. Still have carpet in the room, so..."

Reviewed on Jul 18, 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
$106 nightly
The price is $122 total per night from Aug 9 to Aug 10
$122 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 ...
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! (3,198 reviews)
"Not a lot to say about this property other than our room was stinky and dirty. Our bathroom smelled like urine and our shower looked like it needed a good scrub. Staff was decent."

Reviewed on Jul 19, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$167 nightly
The price is $199 total per night from Aug 19 to Aug 20
$199 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 ...
7.6/10 Good! (2,694 reviews)
"The hotel is conveniently located near many fun attractions and appears to be in a relatively safe area. The staff was polite and courteous throughout my stay. The room layout could have been better, and the hotel itself is dated. The air-conditioning units were also quite loud. My unit displayed ..."

Reviewed on Jul 19, 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 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! (1,986 reviews)
"It's a Motel 6 so expectations shouldn't be too high but this place was pretty aweful. The room was baren. A bed, a tv and a table, not much else. The carpets in the main hallways were pretty dirty. There was a garbage can on the first floor by the ice machine that was overflowing (items on the ground) ..."

Reviewed on Jul 18, 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
$237 nightly
The price is $282 total per night from Aug 9 to Aug 10
$282 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
$241 nightly
The price is $287 total per night from Aug 9 to Aug 10
$287 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 ...
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 Aug 16 to Aug 17
$250 total
Aug 16 - Aug 17
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! (6,014 reviews)
"Everything was amazing and beautiful"

Reviewed on Jul 19, 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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