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

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Cheap Flights from JAN to MDW starting at $128 One Way, $277 Round Trip

Prices starting at $277 for return flights and $128 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 14 - Mon, Oct 19
JAN
Jackson
MDW
Chicago
$277 Roundtrip, found 1 hour ago
$277
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Oct 14 from Jackson to Chicago, returning Mon, Oct 19, priced at $277 found 1 hour ago
Wed, Oct 14 - Mon, Oct 19
JAN
Jackson
MDW
Chicago
$282 Roundtrip, found 1 hour ago
$282
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Oct 14 from Jackson to Chicago, returning Mon, Oct 19, priced at $282 found 1 hour ago
Wed, Oct 14 - Mon, Oct 19
JAN
Jackson
MDW
Chicago
$291 Roundtrip, found 1 hour ago
$291
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Oct 14 from Jackson to Chicago, returning Mon, Oct 19, priced at $291 found 1 hour ago
Wed, Oct 14 - Mon, Oct 19
JAN
Jackson
MDW
Chicago
$297 Roundtrip, found 1 hour ago
$297
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Oct 14 from Jackson to Chicago, returning Mon, Oct 19, priced at $297 found 1 hour ago
Wed, Oct 14 - Mon, Oct 19
JAN
Jackson
MDW
Chicago
$300 Roundtrip, found 1 hour ago
$300
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, Oct 14 from Jackson to Chicago, returning Mon, Oct 19, priced at $300 found 1 hour 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
The price is $188 total per night from Sep 27 to Sep 28
$188 total
per night
Sep 27 - Sep 28
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 ...
8/10 Very Good! (1,002 reviews)
"The rooms were nice and the property was maintained well but that’s it. Customer service was so lousy to the point of almost nonexistence. They don’t offer taxi service and their airport shuttle only runs 8 hours from 7 am to 3 pm. One day they had no one to do the shuttle so I was left to my own ..."

Reviewed on Sep 17, 2026

Holiday Inn Chicago – Midway Airport S by IHG
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is $195 total per night from Sep 27 to Sep 28
$195 total
per night
Sep 27 - Sep 28
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! (10,157 reviews)
"Grand old hotel. Worth seeing … but getting old."

Reviewed on Sep 17, 2026

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
The price is $294 total per night from Sep 25 to Sep 26
$294 total
per night
Sep 25 - Sep 26
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (3,219 reviews)
"Very nice place to stay."

Reviewed on Sep 17, 2026

Hilton 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.

Hotels In Chicago

River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is $208 total per night from Sep 20 to Sep 21
$208 total
per night
Sep 20 - Sep 21
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (5,434 reviews)
"I really love this hotel and is close to everything just walking a couple minutes."

Reviewed on Sep 17, 2026

River 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
The price is $191 total per night from Sep 27 to Sep 28
$191 total
per night
Sep 27 - Sep 28
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! (2,254 reviews)
"The hotel was overbooked so instead of the junior suite I booked and paid for, I was given a standard king with no change in price. The room was also nothing like what it looks like in the pictures. The room was old and lots of stains and damage."

Reviewed on Sep 17, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is $195 total per night from Sep 27 to Sep 28
$195 total
per night
Sep 27 - Sep 28
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! (10,157 reviews)
"Grand old hotel. Worth seeing … but getting old."

Reviewed on Sep 17, 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.

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
The price is $60 total per night from Oct 4 to Oct 5
$60 total
per night
Oct 4 - Oct 5
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
The price is $110 total per night from Oct 18 to Oct 19
$110 total
per night
Oct 18 - Oct 19
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 ...
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
The price is $116 total per night from Oct 4 to Oct 5
$116 total
per night
Oct 4 - Oct 5
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 ...
7.8/10 Good! (3,156 reviews)
"This hotel would be my last option in the O’Hare area. Needs a renovation urgently. Only positive aspect is the Deep Dish Pizza at UNO Pizzeria."

Reviewed on Sep 17, 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
The price is $232 total per night from Sep 27 to Sep 28
$232 total
per night
Sep 27 - Sep 28
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! (3,385 reviews)
"Old hotel, completely uninterested staff. Insane pricing and a room the size of a standard alcove with very little room to unpack or move around. Better than average overall (cool bar, lounge area, etc.), but could use some updates and some attention to detail."

Reviewed on Sep 17, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
The price is $183 total per night from Sep 27 to Sep 28
$183 total
per night
Sep 27 - Sep 28
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 ...
7.8/10 Good! (2,838 reviews)
"Enjoy my stay"

Reviewed on Sep 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
The price is $60 total per night from Oct 4 to Oct 5
$60 total
per night
Oct 4 - Oct 5
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
The price is $301 total per night from Sep 27 to Sep 28
$301 total
per night
Sep 27 - Sep 28
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 ...
8.4/10 Very Good! (2,998 reviews)
"Love the location. Staff polite and helpful. Complimentary daily reception is a nice touch as well as included breakfast ! Great views of the city from the hotel!"

Reviewed on Sep 17, 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 $358 total per night from Sep 27 to Sep 28
$358 total
per night
Sep 27 - Sep 28
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 Sep 20 to Sep 21
$250 total
per night
Sep 20 - Sep 21
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 ...
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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