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

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Cheap Flights from CLT to MDW starting at $91 One Way, $212 Round Trip

Prices starting at $212 for return flights and $91 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.

Fri, Dec 4 - Sun, Dec 6
CLT
Charlotte
MDW
Chicago
$212 Roundtrip, found 18 hours ago
$212
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Fri, Dec 4 from Charlotte to Chicago, returning Sun, Dec 6, priced at $212 found 18 hours ago
Sat, Nov 21 - Wed, Nov 25
CLT
Charlotte
MDW
Chicago
$220 Roundtrip, found 2 days ago
$220
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Nov 21 from Charlotte to Chicago, returning Wed, Nov 25, priced at $220 found 2 days ago
Sat, Nov 14 - Sun, Nov 15
CLT
Charlotte
MDW
Chicago
$224 Roundtrip, found 4 hours ago
$224
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Sat, Nov 14 from Charlotte to Chicago, returning Sun, Nov 15, priced at $224 found 4 hours ago
Mon, Nov 9 - Wed, Nov 11
CLT
Charlotte
MDW
Chicago
$231 Roundtrip, found 6 hours ago
$231
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Mon, Nov 9 from Charlotte to Chicago, returning Wed, Nov 11, priced at $231 found 6 hours ago
Sat, Nov 14 - Sun, Nov 15
CLT
Charlotte
MDW
Chicago
$234 Roundtrip, found 4 hours ago
$234
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Sat, Nov 14 from Charlotte to Chicago, returning Sun, Nov 15, priced at $234 found 4 hours 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
$145 nightly
The price is $168 total per night from Oct 25 to Oct 26
$168 total
Oct 25 - Oct 26
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
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
$107 nightly
The price is $127 total per night from Nov 11 to Nov 12
$127 total
Nov 11 - Nov 12
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! (10,176 reviews)
"The room I stayed in 1270 was terrible maintained. It was clean but shower seemed to have be poorly repaired too many times, toilet was loose and a bit crooked, the door nob on the bathroom door coming off, door on the dresser also crooked and tiles on the bathroom floor broken. The hotel does not ..."

Reviewed on Oct 21, 2026

Congress Plaza Hotel
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
$158 nightly
The price is $188 total per night from Nov 11 to Nov 12
$188 total
Nov 11 - Nov 12
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and ...
Holiday Inn & Suites Chicago - Downtown by IHG
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

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$107 nightly
The price is $127 total per night from Nov 11 to Nov 12
$127 total
Nov 11 - Nov 12
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! (10,176 reviews)
"The room I stayed in 1270 was terrible maintained. It was clean but shower seemed to have be poorly repaired too many times, toilet was loose and a bit crooked, the door nob on the bathroom door coming off, door on the dresser also crooked and tiles on the bathroom floor broken. The hotel does not ..."

Reviewed on Oct 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
$121 nightly
The price is $143 total per night from Nov 11 to Nov 12
$143 total
Nov 11 - Nov 12
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! (2,545 reviews)
"needs a major update. elevator is so tiny and there are chunks out of the wall covered by paint."

Reviewed on Oct 21, 2026

The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$152 nightly
The price is $181 total per night from Nov 1 to Nov 2
$181 total
Nov 1 - Nov 2
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
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
$60 nightly
The price is $68 total per night from Oct 25 to Oct 26
$68 total
Oct 25 - Oct 26
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
$106 nightly
The price is $117 total per night from Oct 28 to Oct 29
$117 total
Oct 28 - Oct 29
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! (1,871 reviews)
"Very disappointing experience. Our room was not ready at the stated check-in time, which was frustrating enough. What made the situation much worse was the attitude of the front desk manager. Instead of apologizing and making a genuine effort to accommodate us while the room was being prepared, the ..."

Reviewed on Oct 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
$101 nightly
The price is $116 total per night from Nov 11 to Nov 12
$116 total
Nov 11 - Nov 12
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! (3,211 reviews)
"The bathtub leaked and they said it wasn’t fixable. One of the beds was broken and the fixed it but broke again. Overall the property is dirty and outdated. 2/10."

Reviewed on Oct 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
$154 nightly
The price is $183 total per night from Nov 3 to Nov 4
$183 total
Nov 3 - Nov 4
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
$120 nightly
The price is $143 total per night from Nov 12 to Nov 13
$143 total
Nov 12 - Nov 13
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
$60 nightly
The price is $68 total per night from Oct 25 to Oct 26
$68 total
Oct 25 - Oct 26
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
$165 nightly
The price is $221 total per night from Nov 1 to Nov 2
$221 total
Nov 1 - Nov 2
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
$215 nightly
The price is $256 total per night from Oct 31 to Nov 1
$256 total
Oct 31 - Nov 1
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! (2,717 reviews)
"Great location. Beautiful historic hotel"

Reviewed on Oct 19, 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
$133 nightly
The price is $181 total per night from Nov 1 to Nov 2
$181 total
Nov 1 - Nov 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! (5,973 reviews)
"Ubicación"

Reviewed on Oct 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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