Cheap flights from CLT to MDW (Charlotte-Douglas Intl. to Midway Intl.)

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Cheap Flights from CLT to MDW starting at $135 One Way, $244 Round Trip

Prices starting at $244 for return flights and $135 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 21 - Mon, Oct 26
CLT
Charlotte
MDW
Chicago
$244 Roundtrip, found 15 hours ago
$244
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Wed, Oct 21 from Charlotte to Chicago, returning Mon, Oct 26, priced at $244 found 15 hours ago
Thu, Sep 10 - Mon, Sep 14
CLT
Charlotte
MDW
Chicago
$247 Roundtrip, found 1 day ago
$247
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Sep 10 from Charlotte to Chicago, returning Mon, Sep 14, priced at $247 found 1 day ago
Wed, Oct 21 - Mon, Oct 26
CLT
Charlotte
MDW
Chicago
$254 Roundtrip, found 15 hours ago
$254
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Wed, Oct 21 from Charlotte to Chicago, returning Mon, Oct 26, priced at $254 found 15 hours ago
Thu, Sep 10 - Mon, Sep 14
CLT
Charlotte
MDW
Chicago
$257 Roundtrip, found 1 day ago
$257
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Sep 10 from Charlotte to Chicago, returning Mon, Sep 14, priced at $257 found 1 day ago
Wed, Oct 21 - Mon, Oct 26
CLT
Charlotte
MDW
Chicago
$259 Roundtrip, found 15 hours ago
$259
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Wed, Oct 21 from Charlotte to Chicago, returning Mon, Oct 26, priced at $259 found 15 hours ago

Hotel Ideas near Midway Intl.

Hotels In Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$135 nightly
The price is $161 total per night from Sep 7 to Sep 8
$161 total
Sep 7 - Sep 8
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! (10,220 reviews)
"The hotel was just across for the Lollapalooza. The A/C wasn’t cool enough for me. My friend got locked in the bathroom when she used the older lock, the door knob looks older too,it took a while to maneuver that so almost call the front desk. Only 3pillows for the king size bed. No coffee maker, ..."

Reviewed on Aug 7, 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
$152 nightly
The price is $181 total per night from Aug 10 to Aug 11
$181 total
Aug 10 - Aug 11
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
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
$212 nightly
The price is $248 total per night from Aug 29 to Aug 30
$248 total
Aug 29 - Aug 30
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 ...
8.4/10 Very Good! (2,373 reviews)
"Comfortable hotel in the airport. Staff is friendly and professional. Restaurant and bar were super congenial. Great place to stay on a quick trip to Chicago or on layover."

Reviewed on Aug 6, 2026

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
$53 nightly
The price is $60 total per night from Sep 1 to Sep 2
$60 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 ...
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
$114 nightly
The price is $126 total per night from Aug 31 to Sep 1
$126 total
Aug 31 - Sep 1
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! (1,656 reviews)
"Arrived after a flight from UK and appreciated having a shuttle bus to take us to the hotel. Following the instructions from the hotel, we only had to wait 45 mins for the transport to arrive at terminal 5 and journey to the hotel took about 20 mins. Family were feeling hungry and reception recommended ..."

Reviewed on Aug 7, 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 1 to Sep 2
$116 total
Sep 1 - Sep 2
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 ...
7.8/10 Good! (3,121 reviews)
"Decent place. Shuttle drivers nice and this free service generally worked out great. One issue one late night from the train of miscommunication but that happens. Easy to get taxi or uber if needed. Good spot for shops and food near hotel. It is a long train ride to the city but that was fine for ..."

Reviewed on Aug 7, 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
$117 nightly
The price is $139 total per night from Aug 31 to Sep 1
$139 total
Aug 31 - Sep 1
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. ...
Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$115 nightly
The price is $137 total per night from Aug 30 to Aug 31
$137 total
Aug 30 - Aug 31
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
$53 nightly
The price is $60 total per night from Sep 1 to Sep 2
$60 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 ...
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
$202 nightly
The price is $241 total per night from Aug 31 to Sep 1
$241 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
$199 nightly
The price is $237 total per night from Sep 7 to Sep 8
$237 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
$161 nightly
The price is $191 total per night from Sep 7 to Sep 8
$191 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! (6,001 reviews)
"The location was great…a little outdated and very busy."

Reviewed on Aug 6, 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.

CLT to MDW Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date
CLT Address & GPS
Address:
5501 Josh Birmingham Parkway
Charlotte NC, 28204
United States
IATA Code:
CLT
Longitude:
-80.935833
Latitude:
35.219167
Time Zone:
America/New_York
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 Charlotte Airport to Chicago Airport?
Listen up. We're about to make your upcoming escape even more exciting. Southwest Airlines flies directly from Charlotte Airport to Chicago Airport, so you'll be starting your next awesome adventure in no time.
What is the shortest flight from Charlotte Airport to Chicago Airport?
Getting from Charlotte Airport to Midway Intl. Airport (MDW) will take a minimum of 4 hours and 48 minutes. Treat yourself to a wine and watch a show or two — this is your chance to just relax.
How many hours flight from Charlotte Airport to Midway Intl. Airport (MDW)?
Don't get too relaxed in your seat — the average flight time from Charlotte Airport to Midway Airport is only 4 hours and 52 minutes.
What airlines have the most flights from Charlotte Airport to Chicago Airport?
One of the leading airlines operating on the CLT to MDW route, Southwest Airlines is the start of your next great adventure. You can select from 49 flights every month with this carrier.

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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