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

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Cheap Flights from CLT to MDW starting at $107 One Way, $212 Round Trip

Prices starting at $212 for return flights and $107 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 5 days ago
$212
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Oct 21 from Charlotte to Chicago, returning Sat, Oct 24, priced at $212 found 5 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 6 days ago
$220
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Dec 5 from Charlotte to Chicago, returning Mon, Dec 7, priced at $220 found 6 days ago
Wed, Oct 21 - Sat, Oct 24
CLT
Charlotte
MDW
Chicago
$222 Roundtrip, found 5 days ago
$222
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Oct 21 from Charlotte to Chicago, returning Sat, Oct 24, priced at $222 found 5 days ago
Wed, Oct 21 - Sat, Oct 24
CLT
Charlotte
MDW
Chicago
$228 Roundtrip, found 5 days ago
$228
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Oct 21 from Charlotte to Chicago, returning Sat, Oct 24, priced at $228 found 5 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! (1,014 reviews)
"amazing and friendly staff"

Reviewed on Sep 22, 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
$201 nightly
The price is $239 total per night from Sep 27 to Sep 28
$239 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 ...
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 Oct 12 to Oct 13
$281 total
Oct 12 - Oct 13
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! (3,277 reviews)
"Rooms are small. Had issue with A/C unit. Had to move three (3) times in the first 24 hours we were there."

Reviewed on Sep 22, 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
$179 nightly
The price is $213 total per night from Sep 27 to Sep 28
$213 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! (5,459 reviews)
"Property is centrally located and staff is over the top accommodating! We’ve stayed two times already. This is our go to hotel in the loop"

Reviewed on Sep 21, 2026

River Hotel
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$201 nightly
The price is $239 total per night from Sep 27 to Sep 28
$239 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 ...
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 ...
8/10 Very Good! (2,300 reviews)
"Carpet was stinky and damp. Very old bathrooms. Not staying there again."

Reviewed on Sep 22, 2026

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
The price is $70 total per night from Oct 4 to Oct 5
$70 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 $110 total per night from Oct 4 to Oct 5
$110 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 ...
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
$224 nightly
The price is $266 total per night from Oct 12 to Oct 13
$266 total
Oct 12 - Oct 13
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! (3,379 reviews)
"There was a spot of blood on our sheets, the shower was covered in mold, the TV did not work, only one plug worked in the room and the ceiling was crumbling on the corner of the room. We were so appalled with our stay we checked out Saturday evening instead of staying and drove home."

Reviewed on Sep 22, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$170 nightly
The price is $200 total per night from Sep 27 to Sep 28
$200 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 ...
7.8/10 Good! (2,864 reviews)
"Easy check-in and out. Staff was nice and helpful. The building was built before a/c was common, but the little window unit worked just fine. I loved the easy walking distance to Grant Park and Michigan Ave. Rooms are clean and neat."

Reviewed on Sep 21, 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
$62 nightly
The price is $70 total per night from Oct 4 to Oct 5
$70 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 ...
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 Oct 1 to Oct 2
$301 total
per night
Oct 1 - Oct 2
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
The price is $377 total per night from Oct 2 to Oct 3
$377 total
per night
Oct 2 - Oct 3
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 $282 total per night from Oct 1 to Oct 2
$282 total
per night
Oct 1 - Oct 2
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! (6,012 reviews)
"Great"

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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