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, $256 Round Trip

Prices starting at $256 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.

Fri, Sep 11 - Mon, Sep 14
CLT
Charlotte
MDW
Chicago
$256 Roundtrip, found 3 days ago
$256
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Fri, Sep 11 from Charlotte to Chicago, returning Mon, Sep 14, priced at $256 found 3 days ago
Sat, Sep 26 - Tue, Sep 29
CLT
Charlotte
MDW
Chicago
$259 Roundtrip, found 4 hours ago
$259
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Sat, Sep 26 from Charlotte to Chicago, returning Tue, Sep 29, priced at $259 found 4 hours ago
Mon, Sep 21 - Thu, Sep 24
CLT
Charlotte
MDW
Chicago
$263 Roundtrip, found 3 hours ago
$263
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Mon, Sep 21 from Charlotte to Chicago, returning Thu, Sep 24, priced at $263 found 3 hours ago
Mon, Aug 17 - Sun, Aug 23
CLT
Charlotte
MDW
Chicago
$266 Roundtrip, found 3 days ago
$266
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Aug 17 from Charlotte to Chicago, returning Sun, Aug 23, priced at $266 found 3 days ago
Sun, Sep 6 - Mon, Sep 14
CLT
Charlotte
MDW
Chicago
$268 Roundtrip, found 5 hours ago
$268
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Sun, Sep 6 from Charlotte to Chicago, returning Mon, Sep 14, priced at $268 found 5 hours ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
$237 nightly
The price is $281 total per night from Aug 9 to Aug 10
$281 total
Aug 9 - Aug 10
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 ...
Hyatt Regency McCormick Place Chicago
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
$175 nightly
The price is $208 total per night from Aug 16 to Aug 17
$208 total
Aug 16 - Aug 17
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
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street Chicago IL
$192 nightly
The price is $228 total per night from Aug 20 to Aug 21
$228 total
Aug 20 - Aug 21
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 in ...
Crowne Plaza Chicago West Loop 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

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
$189 nightly
The price is $215 total per night from Aug 6 to Aug 7
$215 total
Aug 6 - Aug 7
Total with taxes and fees
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,888 reviews)
"Food crumbles on the floor, room nine zero seven"

Reviewed on Jul 24, 2026

Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
$172 nightly
The price is $204 total per night from Aug 3 to Aug 4
$204 total
Aug 3 - Aug 4
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 ...
8.2/10 Very Good! (1,822 reviews)
"Nice large room. Everything was in good shape. There was no coffee maker and no microwave, no snacks, no vending. We needed hot water for tea. The first night, the bar provided such, albeit slowly. The second they refused and were rather brusk about it. This was quite disappointing from an expensive ..."

Reviewed on Jul 24, 2026

The Chicago Hotel Collection Ambassador Gold Coast
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
$149 nightly
The price is $177 total per night from Aug 9 to Aug 10
$177 total
Aug 9 - Aug 10
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
The Wade
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
$65 nightly
The price is $73 total per night from Aug 10 to Aug 11
$73 total
Aug 10 - Aug 11
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 Aug 24 to Aug 25
$110 total
Aug 24 - Aug 25
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! (1,614 reviews)
"We enjoyed our stay at the hotel."

Reviewed on Jul 23, 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
$93 nightly
The price is $107 total per night from Aug 24 to Aug 25
$107 total
Aug 24 - Aug 25
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
$143 nightly
The price is $171 total per night from Aug 10 to Aug 11
$171 total
Aug 10 - Aug 11
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! (3,213 reviews)
"Very much the budget option if you're going to be staying in downtown Chicago. Rooms are kinda small and the building is old. The bed was not very good, but it was okay. Where the hotel loses points though is cleanliness. The bed sheets had visible stains on them that kinda grossed me out. Maybe ..."

Reviewed on Jul 24, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$154 nightly
The price is $183 total per night from Aug 10 to Aug 11
$183 total
Aug 10 - Aug 11
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 ...
7.6/10 Good! (2,700 reviews)
"You get what you pay for. The price of this place was good for my budget, and the location was great. however the air conditioner was loud, positioned poorly which messed up my breathing while trying to sleep, the sheers didn't block out the sun or outside evening lights, towels were cheap and would ..."

Reviewed on Jul 24, 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
$65 nightly
The price is $73 total per night from Aug 10 to Aug 11
$73 total
Aug 10 - Aug 11
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
$194 nightly
The price is $230 total per night from Aug 10 to Aug 11
$230 total
Aug 10 - Aug 11
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! (2,946 reviews)
"Staff was friendly from the front desk, to the bar tender, to the guy making the omelettes at breakfast. Wonderful Stay!!!"

Reviewed on Jul 24, 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
$249 nightly
The price is $297 total per night from Aug 9 to Aug 10
$297 total
Aug 9 - Aug 10
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! (2,536 reviews)
"The charcuterie was great."

Reviewed on Jul 24, 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
$186 nightly
The price is $221 total per night from Aug 9 to Aug 10
$221 total
Aug 9 - Aug 10
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.

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