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 3 days ago
$212
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Oct 21 from Charlotte to Chicago, returning Sat, Oct 24, priced at $212 found 3 days ago
Wed, Oct 14 - Sat, Oct 17
CLT
Charlotte
MDW
Chicago
$219 Roundtrip, found 5 days ago
$219
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Oct 14 from Charlotte to Chicago, returning Sat, Oct 17, priced at $219 found 5 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 3 days ago
$222
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Oct 21 from Charlotte to Chicago, returning Sat, Oct 24, priced at $222 found 3 days ago
Wed, Oct 21 - Sat, Oct 24
CLT
Charlotte
MDW
Chicago
$228 Roundtrip, found 3 days ago
$228
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Oct 21 from Charlotte to Chicago, returning Sat, Oct 24, priced at $228 found 3 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 ...
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! (3,263 reviews)
"Nice older historic property. It is a good place to stay. The settee, or mini couch was not comfortable. I bring my coffee setup from home. They only have disposable cups for use. Ask the front desk for bottled water or two. Large room, I think it was an upgrade, thanks."

Reviewed on Sep 20, 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
$187 nightly
The price is $222 total per night from Sep 27 to Sep 28
$222 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! (5,452 reviews)
"great location, decent amount of space at a reasonable price (for nowadays)"

Reviewed on Sep 20, 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 ...
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 Sep 21 to Sep 22
$213 total
Sep 21 - Sep 22
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 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! (2,011 reviews)
"Muy limpio y muy Traquilo genial volvería a quedarme otra vez o la veces que desee"

Reviewed on Sep 20, 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 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 ...
7.6/10 Good! (1,778 reviews)
"Great breakfast clean room would stay again"

Reviewed on Sep 20, 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
$100 nightly
The price is $115 total per night from Oct 4 to Oct 5
$115 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! (3,173 reviews)
"Good eggs lol"

Reviewed on Sep 20, 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 12 to Oct 13
$268 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. ...
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 $202 total per night from Sep 27 to Sep 28
$202 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! (2,857 reviews)
"Property location is walkable to Grant Park. The hotel is in need of an upgrade but if you can get past that it is very clean and safe. Our room faced the front and even though on the 12th floor you could hear the train all night long. The curtain in the room did not completely cover the window so ..."

Reviewed on Sep 20, 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! (2,011 reviews)
"Muy limpio y muy Traquilo genial volvería a quedarme otra vez o la veces que desee"

Reviewed on Sep 20, 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
$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! (3,008 reviews)
"Everything was very nice. The breakfast set up was very well put together but the eggs were less desirable. Of course that’s my opinion."

Reviewed on Sep 20, 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
$309 nightly
The price is $367 total per night from Sep 27 to Sep 28
$367 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! (2,660 reviews)
"Wonderful and beautiful hotel! I highly recommend for a historical downtown stay in the heart of Chicago!"

Reviewed on Sep 20, 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
$217 nightly
The price is $258 total per night from Sep 27 to Sep 28
$258 total
Sep 27 - Sep 28
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! (6,009 reviews)
"Breakfast was amazing. Loved the made to order omelets. We also were able to enjoy happy hour. The hotel was clean, conveniently located.and felt very secure."

Reviewed on Sep 20, 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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