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

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Cheap Flights from CLT to MDW starting at $106 One Way, $259 Round Trip

Prices starting at $259 for return flights and $106 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.

Thu, Nov 26 - Fri, Dec 4
CLT
Charlotte
MDW
Chicago
$259 Roundtrip, found 2 days ago
$259
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Nov 26 from Charlotte to Chicago, returning Fri, Dec 4, priced at $259 found 2 days ago
Thu, Dec 10 - Fri, Dec 11
CLT
Charlotte
MDW
Chicago
$264 Roundtrip, found 6 days ago
$264
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Dec 10 from Charlotte to Chicago, returning Fri, Dec 11, priced at $264 found 6 days ago
Mon, Oct 19 - Wed, Oct 21
CLT
Charlotte
MDW
Chicago
$267 Roundtrip, found 4 days ago
$267
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Mon, Oct 19 from Charlotte to Chicago, returning Wed, Oct 21, priced at $267 found 4 days ago
Fri, Dec 11 - Sun, Dec 13
CLT
Charlotte
MDW
Chicago
$280 Roundtrip, found 6 days ago
$280
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Fri, Dec 11 from Charlotte to Chicago, returning Sun, Dec 13, priced at $280 found 6 days ago
Fri, Oct 16 - Mon, Oct 19
CLT
Charlotte
MDW
Chicago
$281 Roundtrip, found 4 days ago
$281
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Fri, Oct 16 from Charlotte to Chicago, returning Mon, Oct 19, priced at $281 found 4 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
$162 nightly
The price is $188 total per night from Sep 27 to Sep 28
$188 total
Sep 27 - Sep 28
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 ...
8/10 Very Good! (1,011 reviews)
"It was incredibly noisy between other guest, staff, and outside all at 1 am. I finally had enough and just checked out and left. Slept in the rental until it was time for my flight"

Reviewed on Sep 14, 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
$164 nightly
The price is $195 total per night from Sep 27 to Sep 28
$195 total
Sep 27 - Sep 28
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! (10,244 reviews)
"Easy check in, rooms were clean, convenient location."

Reviewed on Sep 14, 2026

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
$252 nightly
The price is $300 total per night from Sep 25 to Sep 26
$300 total
Sep 25 - Sep 26
Total with taxes and fees
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! (3,209 reviews)
"Great stay!"

Reviewed on Sep 14, 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
$154 nightly
The price is $183 total per night from Sep 27 to Sep 28
$183 total
Sep 27 - Sep 28
Total with taxes and fees
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 ...
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
$179 nightly
The price is $213 total per night from Oct 13 to Oct 14
$213 total
Oct 13 - Oct 14
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
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$164 nightly
The price is $195 total per night from Sep 27 to Sep 28
$195 total
Sep 27 - Sep 28
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! (10,244 reviews)
"Easy check in, rooms were clean, convenient location."

Reviewed on Sep 14, 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
$53 nightly
The price is $60 total per night from Oct 4 to Oct 5
$60 total
Oct 4 - Oct 5
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! (2,010 reviews)
"Clean room and friendly staff, outside area feels safe. I think these are the most important. Downside is no refrigerator in room. No microwave in room either but there is one in lobby downstairs."

Reviewed on Sep 14, 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
$100 nightly
The price is $110 total per night from Oct 4 to Oct 5
$110 total
Oct 4 - Oct 5
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 ...
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 Oct 4 to Oct 5
$116 total
Oct 4 - Oct 5
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! (3,165 reviews)
"I would have thought that if you stayed at the hotel your parking would be free."

Reviewed on Sep 14, 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
$226 nightly
The price is $268 total per night from Oct 6 to Oct 7
$268 total
Oct 6 - Oct 7
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! (3,369 reviews)
"This hotel has a great location, but not much more. My room was tiny, the AC kept switching on & off by itself, and they don't serve breakfast, not even morning coffee (or if they do, nobody told me & I couldn't find it). On the other hand, the lobby/lounge decor is quite nice, but the one time I ..."

Reviewed on Sep 14, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$153 nightly
The price is $180 total per night from Sep 27 to Sep 28
$180 total
Sep 27 - Sep 28
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! (2,844 reviews)
"Buena ubicación, personal muy atento y cortés. Muy cerca de Millenium Park. Las habitaciones necesitan unidad de aire acondicionado con más potencia."

Reviewed on Sep 13, 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
$53 nightly
The price is $60 total per night from Oct 4 to Oct 5
$60 total
Oct 4 - Oct 5
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! (2,010 reviews)
"Clean room and friendly staff, outside area feels safe. I think these are the most important. Downside is no refrigerator in room. No microwave in room either but there is one in lobby downstairs."

Reviewed on Sep 14, 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
$262 nightly
The price is $311 total per night from Sep 20 to Sep 21
$311 total
Sep 20 - Sep 21
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
$288 nightly
The price is $342 total per night from Sep 20 to Sep 21
$342 total
Sep 20 - Sep 21
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 ...
8.6/10 Excellent! (2,644 reviews)
"Beautiful, historic hotel. The staff are all very nice and helpful. The exercise facility was the best I’ve ever seen with multiple rooms, peloton bikes, and so much equipment. The women’s locker room even had a dry sauna. They said they weren’t known for their views, but our room on the 22nd floor ..."

Reviewed on Sep 14, 2026

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
$195 nightly
The price is $231 total per night from Sep 20 to Sep 21
$231 total
Sep 20 - Sep 21
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! (6,007 reviews)
"Muy tranquilo seguro,limpio todon muy bien lo recomiendo 10de10"

Reviewed on Sep 13, 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.

More to Explore