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

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Cheap Flights from CLT to MDW starting at $105 One Way, $212 Round Trip

Prices starting at $212 for return flights and $105 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 - Sat, Oct 24
CLT
Charlotte
MDW
Chicago
$212 Roundtrip, found 4 days ago
$212
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Oct 21 from Charlotte to Chicago, returning Sat, Oct 24, priced at $212 found 4 days ago
Wed, Oct 14 - Sat, Oct 17
CLT
Charlotte
MDW
Chicago
$219 Roundtrip, found 6 days ago
$219
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Oct 14 from Charlotte to Chicago, returning Sat, Oct 17, priced at $219 found 6 days ago
Sat, Dec 5 - Mon, Dec 7
CLT
Charlotte
MDW
Chicago
$220 Roundtrip, found 5 days ago
$220
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Dec 5 from Charlotte to Chicago, returning Mon, Dec 7, priced at $220 found 5 days ago
Wed, Oct 21 - Sat, Oct 24
CLT
Charlotte
MDW
Chicago
$222 Roundtrip, found 4 days ago
$222
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Oct 21 from Charlotte to Chicago, returning Sat, Oct 24, priced at $222 found 4 days ago
Wed, Oct 21 - Sat, Oct 24
CLT
Charlotte
MDW
Chicago
$228 Roundtrip, found 4 days ago
$228
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Oct 21 from Charlotte to Chicago, returning Sat, Oct 24, priced at $228 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 ...
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
$178 nightly
The price is $212 total per night from Sep 27 to Sep 28
$212 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! (10,177 reviews)
"Beautiful building and a great stay. I had a lake view room and this was my second time staying here!"

Reviewed on Sep 21, 2026

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
$236 nightly
The price is $281 total per night from Sep 27 to Sep 28
$281 total
Sep 27 - Sep 28
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! (3,271 reviews)
"We loved the historic aspects of the hotel. It takes up an entire city block and is packed with so much history celebrating nearly 100 years in business. However that comes with the downside of lower ceilings, older rooms, etc. the room was small but very clean and reasonable, I just prefer something ..."

Reviewed on Sep 21, 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
$189 nightly
The price is $224 total per night from Sep 27 to Sep 28
$224 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 ...
8.8/10 Excellent! (5,454 reviews)
"Too expensive for nothing. Even the keys need to be made ourselves and not by the staff. Hostel kind of feel at luxury hotel prices."

Reviewed on Sep 21, 2026

River Hotel
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$178 nightly
The price is $212 total per night from Sep 27 to Sep 28
$212 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! (10,177 reviews)
"Beautiful building and a great stay. I had a lake view room and this was my second time staying here!"

Reviewed on Sep 21, 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
$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
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 19 to Oct 20
$60 total
Oct 19 - Oct 20
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
$100 nightly
The price is $110 total per night from Oct 18 to Oct 19
$110 total
Oct 18 - Oct 19
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
$96 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 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! (3,176 reviews)
"The mirror fell off the wall as soon as we closed our hotel room door. There was fresh blood dropping on the elevator floor. The bathroom floor was sticky."

Reviewed on Sep 21, 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 7 to Oct 8
$268 total
Oct 7 - Oct 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! (3,377 reviews)
"The location and the price of this hotel are excellent. The attached café and bar were very nice for breakfast and drinks. Check-in was quick and the front desk staff Dana was kind and helpful. The rooms are very compact and dated. And while the bathroom was very small, it was very clean and well ..."

Reviewed on Sep 21, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$157 nightly
The price is $185 total per night from Sep 27 to Sep 28
$185 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 ...
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 19 to Oct 20
$60 total
Oct 19 - Oct 20
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
$253 nightly
The price is $301 total per night from Sep 27 to Sep 28
$301 total
Sep 27 - Sep 28
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 ...
8.2/10 Very Good! (3,011 reviews)
"The bathroom had mold around the tub and in the grout. No exhaust fan in bathroom. Sofa had stains on it."

Reviewed on Sep 21, 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
$284 nightly
The price is $338 total per night from Sep 27 to Sep 28
$338 total
Sep 27 - Sep 28
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! (2,661 reviews)
"Love the Palmer House. From the moment you walk in the front door you feel special. Check in was a breeze. The gym and pool were exceptional. Don’t think I’ve seen a better hotel gym than at the Palmer House. Loved Potter’s Bar. Had the best Old Fashioned there. About my only complaint was the room ..."

Reviewed on Sep 21, 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
$207 nightly
The price is $282 total per night from Oct 1 to Oct 2
$282 total
Oct 1 - Oct 2
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! (6,011 reviews)
"1) Noisy location… 2) Closet door was hanging off hinges 3) Would classify the website info on hotel amenities as very poor. Details on hours for Pool and exercise room were non existent. No booklet with details in the room. Went to hotel info screen on the TV and there was nothing there either, ..."

Reviewed on Sep 21, 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

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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