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

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Cheap Flights from JAN to MDW starting at $129 One Way, $295 Round Trip

Prices starting at $295 for return flights and $129 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, Sep 2 - Fri, Sep 4
JAN
Jackson
MDW
Chicago
$295 Roundtrip, found 5 days ago
$295
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Sep 2 from Jackson to Chicago, returning Fri, Sep 4, priced at $295 found 5 days ago
Fri, Oct 2 - Mon, Oct 5
JAN
Jackson
MDW
Chicago
$296 Roundtrip, found 6 days ago
$296
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Fri, Oct 2 from Jackson to Chicago, returning Mon, Oct 5, priced at $296 found 6 days ago
Wed, Sep 2 - Fri, Sep 4
JAN
Jackson
MDW
Chicago
$301 Roundtrip, found 5 days ago
$301
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Sep 2 from Jackson to Chicago, returning Fri, Sep 4, priced at $301 found 5 days ago
Fri, Oct 2 - Mon, Oct 5
JAN
Jackson
MDW
Chicago
$307 Roundtrip, found 6 days ago
$307
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Fri, Oct 2 from Jackson to Chicago, returning Mon, Oct 5, priced at $307 found 6 days ago
Wed, Sep 2 - Fri, Sep 4
JAN
Jackson
MDW
Chicago
$312 Roundtrip, found 5 days ago
$312
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Sep 2 from Jackson to Chicago, returning Fri, Sep 4, priced at $312 found 5 days ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
7353 S Cicero Avenue Chicago IL
$124 nightly
The price is $144 total per night from Sep 8 to Sep 9
$144 total
Sep 8 - Sep 9
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 and ...
Holiday Inn Chicago – Midway Airport S by IHG
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
$211 nightly
The price is $251 total per night from Sep 1 to Sep 2
$251 total
Sep 1 - Sep 2
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
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$115 nightly
The price is $136 total per night from Sep 8 to Sep 9
$136 total
Sep 8 - Sep 9
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! (10,248 reviews)
"The hotel is in a great location right across from Grant Park but the hotel is really dated. I usually love a historic hotel… but this one needs a little love. Our room was “ok”… everything worked and we didn’t have any issues but it was just old and felt old. I wouldn’t stay here again. If you do ..."

Reviewed on Aug 18, 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
$115 nightly
The price is $136 total per night from Sep 8 to Sep 9
$136 total
Sep 8 - Sep 9
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! (10,248 reviews)
"The hotel is in a great location right across from Grant Park but the hotel is really dated. I usually love a historic hotel… but this one needs a little love. Our room was “ok”… everything worked and we didn’t have any issues but it was just old and felt old. I wouldn’t stay here again. If you do ..."

Reviewed on Aug 18, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
$143 nightly
The price is $170 total per night from Aug 30 to Aug 31
$170 total
Aug 30 - Aug 31
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 ...
8/10 Very Good! (2,029 reviews)
"Very friendly and professional staff. Building does show its age though."

Reviewed on Aug 18, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
$239 nightly
The price is $281 total per night from Sep 12 to Sep 13
$281 total
Sep 12 - Sep 13
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
Hilton 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.

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
$57 nightly
The price is $65 total per night from Sep 1 to Sep 2
$65 total
Sep 1 - Sep 2
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! (2,008 reviews)
"No toiletries"

Reviewed on Aug 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
$109 nightly
The price is $120 total per night from Sep 8 to Sep 9
$120 total
Sep 8 - Sep 9
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! (1,699 reviews)
"Unfortunately, my experience was very disappointing. The staff member I encountered was not friendly or welcoming. When I approached her, she told me to “take a seat” because she was doing something more important, which felt dismissive and unprofessional. The room itself was dark, dingy, and had ..."

Reviewed on Aug 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
$101 nightly
The price is $116 total per night from Sep 7 to Sep 8
$116 total
Sep 7 - Sep 8
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
$120 nightly
The price is $143 total per night from Sep 7 to Sep 8
$143 total
Sep 7 - Sep 8
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! (3,328 reviews)
"Quad room equipped with iron, safe, lockers and towels/linens. Perfect location for a girls trip. Room A/C worked great, hot water, friendly service from staff. Great value! CVS conveniently right next door. Could use some extra mirrors in the room."

Reviewed on Aug 18, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$107 nightly
The price is $127 total per night from Aug 31 to Sep 1
$127 total
Aug 31 - Sep 1
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! (2,775 reviews)
"Very dated property. A bit rundown and not all that clean. Very good location however."

Reviewed on Aug 17, 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
$57 nightly
The price is $65 total per night from Sep 1 to Sep 2
$65 total
Sep 1 - Sep 2
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! (2,008 reviews)
"No toiletries"

Reviewed on Aug 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
$170 nightly
The price is $228 total per night from Aug 31 to Sep 1
$228 total
Aug 31 - Sep 1
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
$198 nightly
The price is $236 total per night from Sep 7 to Sep 8
$236 total
Sep 7 - Sep 8
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
$152 nightly
The price is $181 total per night from Sep 7 to Sep 8
$181 total
Sep 7 - Sep 8
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! (6,030 reviews)
"Very clean. Attention need in your room."

Reviewed on Aug 18, 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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