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

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Cheap Flights from JAN to MDW starting at $142 One Way, $197 Round Trip

Prices starting at $197 for return flights and $142 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.

Sat, Jun 7 - Sat, Jun 14
JAN
Jackson
MDW
Chicago
$197 Roundtrip, found 2 hours ago
$197
Roundtrip
found 2 hours ago
Select Delta flight, departing Sat, Jun 7 from Jackson to Chicago, returning Sat, Jun 14, priced at $197 found 2 hours ago
Tue, Jun 3 - Sat, Jun 14
JAN
Jackson
MDW
Chicago
$200 Roundtrip, found 2 hours ago
$200
Roundtrip
found 2 hours ago
Select Delta flight, departing Tue, Jun 3 from Jackson to Chicago, returning Sat, Jun 14, priced at $200 found 2 hours ago
Sat, Jun 7 - Thu, Jun 12
JAN
Jackson
MDW
Chicago
$242 Roundtrip, found 2 hours ago
$242
Roundtrip
found 2 hours ago
Select Delta flight, departing Sat, Jun 7 from Jackson to Chicago, returning Thu, Jun 12, priced at $242 found 2 hours ago
Tue, Jun 3 - Thu, Jun 12
JAN
Jackson
MDW
Chicago
$246 Roundtrip, found 2 hours ago
$246
Roundtrip
found 2 hours ago
Select Delta flight, departing Tue, Jun 3 from Jackson to Chicago, returning Thu, Jun 12, priced at $246 found 2 hours ago
Sat, Jul 5 - Tue, Jul 8
JAN
Jackson
MDW
Chicago
$257 Roundtrip, found 6 days ago
$257
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Jul 5 from Jackson to Chicago, returning Tue, Jul 8, priced at $257 found 6 days ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

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
The price is $133 per night from May 27 to May 28
$133
includes taxes & fees
$113 per night
May 27 - May 28
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
8.8/10 Excellent! (1,020 reviews)
"Satisfied with the overall stay."

Reviewed on May 4, 2025

Crowne Plaza Chicago West Loop by IHG
Holiday Inn & Suites Chicago - Downtown by IHG
Holiday Inn & Suites Chicago - Downtown by IHG
3 out of 5
506 West Harrison Street, Chicago, IL
The price is $139 per night from May 26 to May 27
$139
includes taxes & fees
$118 per night
May 26 - May 27
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8/10 Very Good! (1,006 reviews)
"Price was right. Close to Union Station. Large cockroach on shower curtain. I knocked it in tub and flushed it down the drain."

Reviewed on May 5, 2025

Holiday Inn & Suites Chicago - Downtown by IHG
Sonder South Wabash
Sonder South Wabash
3.5 out of 5
1419 South Wabash Avenue, Chicago, IL
The price is $126 per night from May 27 to May 28
$126
includes taxes & fees
$108 per night
May 27 - May 28
Stay at this 3.5-star aparthotel in Chicago. Enjoy a fitness center, concierge services, and in-room washers/dryers. Popular attractions Soldier Field and Grant ...
8.8/10 Excellent! (492 reviews)
"I absolutely llloovveeedddd our stay! It was a little difficult to find and parking was kind of annoying but the place was in the perfect spot. It was so clean and spacious, the balcony was beautiful and we loved alll of the windows. Absolutely blown away, will definitely stay here again!"

Reviewed on May 5, 2025

Sonder South Wabash
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
The price is $157 per night from May 13 to May 14
$157
includes taxes & fees
$133 per night
May 13 - May 14
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,766 reviews)
"Great location to explore from. Good value."

Reviewed on May 5, 2025

Congress Plaza 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 $199 per night from May 27 to May 28
$199
includes taxes & fees
$169 per night
May 27 - May 28
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.2/10 Very Good! (4,007 reviews)
"Very happy with my stay at Embassy Suite, would have given 5 stars if the hotel parking wasn’t so expensive."

Reviewed on May 6, 2025

Embassy Suites by Hilton Chicago Downtown River North
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
The price is $179 per night from May 11 to May 12
$179
includes taxes & fees
$152 per night
May 11 - May 12
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,193 reviews)
"Great location with proximity to the Magnificent Mile."

Reviewed on May 5, 2025

Hilton Chicago/Magnificent Mile Suites
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 $48 per night from May 14 to May 15
$48
includes taxes & fees
$42 per night
May 14 - May 15
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! (1,437 reviews)
"Excellent staff! Especially Perla the housekeeper lady is so nice."

Reviewed on May 6, 2025

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 $96 per night from Jun 4 to Jun 5
$96
includes taxes & fees
$87 per night
Jun 4 - Jun 5
Stay at this 3-star golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
6.8/10 (1,010 reviews)
"The ac doesn’t work properly"

Reviewed on May 5, 2025

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 $102 per night from May 11 to May 12
$102
includes taxes & fees
$89 per night
May 11 - May 12
Stay at this 3-star 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! (2,471 reviews)
"It was a great stay"

Reviewed on May 6, 2025

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 $117 per night from May 26 to May 27
$117
includes taxes & fees
$100 per night
May 26 - May 27
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
7.8/10 Good! (1,763 reviews)
"Affordable, in the city and the red line is right there."

Reviewed on May 5, 2025

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 $100 per night from May 11 to May 12
$100
includes taxes & fees
$86 per night
May 11 - May 12
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 ...
7/10 Good! (2,126 reviews)
"Great stay"

Reviewed on May 3, 2025

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 $48 per night from May 14 to May 15
$48
includes taxes & fees
$42 per night
May 14 - May 15
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! (1,437 reviews)
"Excellent staff! Especially Perla the housekeeper lady is so nice."

Reviewed on May 6, 2025

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 $210 per night from May 12 to May 13
$210
includes taxes & fees
$179 per night
May 12 - May 13
Stay at this 4-star 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! (2,659 reviews)
Great place
"Friendly and helpful staff. Had a great stay. Bathroom could use more ventilation but overall a great place. And very convenient location"

Reviewed on May 3, 2025

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 $192 per night from May 26 to May 27
$192
includes taxes & fees
$167 per night
May 26 - May 27
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,710 reviews)
"Near the art institute and all of the Loop attractions. Very nice staff."

Reviewed on May 3, 2025

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 $199 per night from May 27 to May 28
$199
includes taxes & fees
$169 per night
May 27 - May 28
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.2/10 Very Good! (4,007 reviews)
"Very happy with my stay at Embassy Suite, would have given 5 stars if the hotel parking wasn’t so expensive."

Reviewed on May 6, 2025

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

Am I able to catch a flight from Jackson, MS Airport (JAN-Evers Intl.) to Chicago, IL Airport (MDW-Midway Intl.) now?
If you’re wondering about travel restrictions and quarantine requirements when flying from Jackson, MS Airport (JAN-Evers Intl.) to Chicago, IL Airport (MDW-Midway Intl.), go right to our Covid-19 Travel Advisor.
Are there non-stop flights from Evers Intl. Airport (JAN) to Midway Intl. Airport (MDW)?
If you’re thinking of flying from Evers Intl. Airport (JAN) to Midway Intl. Airport (MDW), get set to change planes. Southwest Airlines, Delta and Aeromexico are airlines that service this route with just one stopover. Use the layover to stretch out your legs and get a bite to eat.
What is the shortest flight from JAN to Chicago Airport?
From Downtown Jackson, the wonderful sights and sounds of West Lawn are 3 hours and 47 minutes away. Book your favorite seat, or perhaps even one with extra legroom, and travel to your destination in total comfort.
How many hours flight from Jackson, MS Airport (JAN-Evers Intl.) to Midway Intl. Airport (MDW)?
From JAN to MDW, you’ll be in the sky for an average of 3 hours and 52 minutes. Sit back, order a glass of wine and put on your noise-canceling headphones. It’s time to binge-watch your favorite TV shows.
If I am not able to travel due to COVID-19, can I cancel my flight to Chicago, IL Airport (MDW-Midway Intl.)?
We get that traveling right now has its challenges, so it’s good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Chicago, IL Airport (MDW-Midway Intl.) have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you’ll quickly see what options are available. Our Customer Service Portal is the place to go for more information.
Are there flights to Chicago, IL Airport (MDW-Midway Intl.) with flexible change policies?
In most cases you’ll have the option to reschedule your flight to Chicago, IL Airport (MDW-Midway Intl.) without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the “no change fees” filter and book with confidence.
What airlines have the most flights from Evers Intl. Airport (JAN) to Chicago Airport?
If you’re wanting to book with an airline that operates direct flights from JAN to Midway Intl. Airport (MDW), you won’t have much luck. You’ll have to make at least one stop to get to your destination.

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.