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 $135 One Way, $273 Round Trip

Prices starting at $273 for return flights and $135 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, Sep 23 - Fri, Sep 25
CLT
Charlotte
MDW
Chicago
$273 Roundtrip, found 6 days ago
$273
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Sep 23 from Charlotte to Chicago, returning Fri, Sep 25, priced at $273 found 6 days ago
Sat, Sep 26 - Mon, Sep 28
CLT
Charlotte
MDW
Chicago
$297 Roundtrip, found 3 hours ago
$297
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Sat, Sep 26 from Charlotte to Chicago, returning Mon, Sep 28, priced at $297 found 3 hours ago
Thu, Sep 10 - Fri, Sep 11
CLT
Charlotte
MDW
Chicago
$298 Roundtrip, found 2 days ago
$298
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Sep 10 from Charlotte to Chicago, returning Fri, Sep 11, priced at $298 found 2 days ago
Sat, Oct 31 - Mon, Nov 2
CLT
Charlotte
MDW
Chicago
$306 Roundtrip, found 5 days ago
$306
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Oct 31 from Charlotte to Chicago, returning Mon, Nov 2, priced at $306 found 5 days ago
Thu, Dec 10 - Mon, Dec 14
CLT
Charlotte
MDW
Chicago
$308 Roundtrip, found 3 days ago
$308
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Dec 10 from Charlotte to Chicago, returning Mon, Dec 14, priced at $308 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
$137 nightly
The price is $159 total per night from Sep 7 to Sep 8
$159 total
Sep 7 - Sep 8
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 ...
8.2/10 Very Good! (1,007 reviews)
"We arrived super late and the front desk was exceptional! Amazing stay! 10/10 will return to this hotel on our next visit"

Reviewed on Aug 28, 2026

Holiday Inn Chicago – Midway Airport S by IHG
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
$234 nightly
The price is $278 total per night from Aug 30 to Aug 31
$278 total
Aug 30 - Aug 31
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,330 reviews)
"Great spot highly recommend"

Reviewed on Aug 29, 2026

Hyatt Regency McCormick Place Chicago
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$117 nightly
The price is $140 total per night from Sep 8 to Sep 9
$140 total
Sep 8 - Sep 9
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! (10,203 reviews)
"The hotel is old and needs a renovation. Carpets are worn and dirty, and you can tell that it hasn't had a refresh in 30+ years. However, we left important medicine behind and we coordinated with them to have it sent to us at our next stop...they were VERY helpful in this regard so despite a negative ..."

Reviewed on Aug 29, 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.

Hotels In Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$117 nightly
The price is $140 total per night from Sep 8 to Sep 9
$140 total
Sep 8 - Sep 9
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! (10,203 reviews)
"The hotel is old and needs a renovation. Carpets are worn and dirty, and you can tell that it hasn't had a refresh in 30+ years. However, we left important medicine behind and we coordinated with them to have it sent to us at our next stop...they were VERY helpful in this regard so despite a negative ..."

Reviewed on Aug 29, 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
$134 nightly
The price is $159 total per night from Aug 30 to Aug 31
$159 total
Aug 30 - Aug 31
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
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
$233 nightly
The price is $273 total per night from Sep 18 to Sep 19
$273 total
Sep 18 - Sep 19
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
Hilton 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.

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
$57 nightly
The price is $65 total per night from Sep 21 to Sep 22
$65 total
Sep 21 - Sep 22
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 Sep 7 to Sep 8
$117 total
Sep 7 - Sep 8
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
$93 nightly
The price is $107 total per night from Sep 28 to Sep 29
$107 total
Sep 28 - Sep 29
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 ...
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
$193 nightly
The price is $229 total per night from Sep 1 to Sep 2
$229 total
Sep 1 - Sep 2
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
$123 nightly
The price is $146 total per night from Aug 30 to Aug 31
$146 total
Aug 30 - Aug 31
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
$57 nightly
The price is $65 total per night from Sep 21 to Sep 22
$65 total
Sep 21 - Sep 22
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
$184 nightly
The price is $218 total per night from Sep 1 to Sep 2
$218 total
Sep 1 - Sep 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 ...
8.2/10 Very Good! (2,972 reviews)
"As a family of five, we stayed for four nights and had a great experience. We really enjoyed both the hotel and its convenient location. The hotel was comfortable and pleasant, making our stay enjoyable for the whole family."

Reviewed on Aug 29, 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
$207 nightly
The price is $246 total per night from Sep 7 to Sep 8
$246 total
Sep 7 - Sep 8
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! (2,600 reviews)
"Beautiful hotel with lots of personality and charm. Great staff, great location, lots of options for food easily available."

Reviewed on Aug 29, 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
$152 nightly
The price is $181 total per night from Sep 7 to Sep 8
$181 total
Sep 7 - Sep 8
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 ...
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