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

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Cheap Flights from CLT to MDW starting at $129 One Way, $259 Round Trip

Prices starting at $259 for return flights and $129 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.

Sat, Sep 5 - Tue, Sep 15
CLT
Charlotte
MDW
Chicago
$259 Roundtrip, found 1 day ago
$259
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Sep 5 from Charlotte to Chicago, returning Tue, Sep 15, priced at $259 found 1 day ago
Sat, Jun 27 - Tue, Jun 30
CLT
Charlotte
MDW
Chicago
$264 Roundtrip, found 6 days ago
$264
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Jun 27 from Charlotte to Chicago, returning Tue, Jun 30, priced at $264 found 6 days ago
Fri, Jul 3 - Wed, Jul 8
CLT
Charlotte
MDW
Chicago
$265 Roundtrip, found 5 days ago
$265
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Fri, Jul 3 from Charlotte to Chicago, returning Wed, Jul 8, priced at $265 found 5 days ago
Wed, Sep 23 - Sat, Sep 26
CLT
Charlotte
MDW
Chicago
$269 Roundtrip, found 2 days ago
$269
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Sep 23 from Charlotte to Chicago, returning Sat, Sep 26, priced at $269 found 2 days ago
Fri, Aug 14 - Sun, Aug 16
CLT
Charlotte
MDW
Chicago
$270 Roundtrip, found 4 hours ago
$270
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Fri, Aug 14 from Charlotte to Chicago, returning Sun, Aug 16, priced at $270 found 4 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
$208 nightly
The price is $247 total per night from Jul 2 to Jul 3
$247 total
Jul 2 - Jul 3
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! (1,094 reviews)
"M"

Reviewed on Jun 1, 2026

Hyatt Regency McCormick Place Chicago
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
$174 nightly
The price is $207 total per night from Jun 28 to Jun 29
$207 total
Jun 28 - Jun 29
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 ...
9/10 Wonderful! (2,235 reviews)
"ok"

Reviewed on Jun 1, 2026

Crowne Plaza Chicago West Loop by IHG
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$145 nightly
The price is $173 total per night from Jun 29 to Jun 30
$173 total
Jun 29 - Jun 30
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! (10,156 reviews)
"Older hotel but well maintained. Rooms took a bit to cool off during the summer but the view was great!"

Reviewed on Jun 2, 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
$145 nightly
The price is $173 total per night from Jun 29 to Jun 30
$173 total
Jun 29 - Jun 30
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! (10,156 reviews)
"Older hotel but well maintained. Rooms took a bit to cool off during the summer but the view was great!"

Reviewed on Jun 2, 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
$154 nightly
The price is $183 total per night from Jun 28 to Jun 29
$183 total
Jun 28 - Jun 29
Total with taxes and fees
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,507 reviews)
"The room wasn't clean when we entered. There was no fitted sheet on the bed. There were water stains on the ceiling."

Reviewed on Jun 2, 2026

The Chicago Hotel Collection - Magnificent Mile
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
$203 nightly
The price is $242 total per night from Jun 30 to Jul 1
$242 total
Jun 30 - Jul 1
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
9.4/10 Exceptional! (4,320 reviews)
"Excellent location and good selection of breakfast"

Reviewed on Jun 2, 2026

Hotel Riu Plaza 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.

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 Jun 25 to Jun 26
$73 total
Jun 25 - Jun 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 ...
7.8/10 Good! (1,946 reviews)
"The floor felt like I was going to fall through. My feet turned black from dirty floor. Doors looked like they had been water damage. The top bed blanket was dirty. For the price I paid, should of had a mIcrowave and refrigerator included."

Reviewed on Jun 1, 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
$103 nightly
The price is $114 total per night from Jun 30 to Jul 1
$114 total
Jun 30 - Jul 1
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! (1,462 reviews)
"It was a great stay!"

Reviewed on Jun 1, 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
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 ...
8/10 Very Good! (3,019 reviews)
"Best value. This Comfort Suites is clean and reasonably priced. Staff is friendly and helpful. They provide a breakfast bar (good for coffee and a pastry) and on site Uno's restaurant. There is an Alidi grocery store and Dollar Tree behind the hotel that you can walk to for essentials. Rooms have ..."

Reviewed on Jun 2, 2026

Get rates
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
$134 nightly
The price is $159 total per night from Jun 29 to Jun 30
$159 total
Jun 29 - Jun 30
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. ...
8/10 Very Good! (3,048 reviews)
"Good stay during a busy weekend. A bit over priced, but I think the event effected the increased cost. Good safe clean stay in a pinch, but definitely a no-frills stay."

Reviewed on Jun 2, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$134 nightly
The price is $159 total per night from Jun 28 to Jun 29
$159 total
Jun 28 - Jun 29
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 ...
7.4/10 Good! (2,618 reviews)
"The room was clean although pretty outdated. The staff was helpful and polite."

Reviewed on May 31, 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 Jun 25 to Jun 26
$73 total
Jun 25 - Jun 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 ...
7.8/10 Good! (1,946 reviews)
"The floor felt like I was going to fall through. My feet turned black from dirty floor. Doors looked like they had been water damage. The top bed blanket was dirty. For the price I paid, should of had a mIcrowave and refrigerator included."

Reviewed on Jun 1, 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 $300 total per night from Jun 28 to Jun 29
$300 total
Jun 28 - Jun 29
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! (2,864 reviews)
"Excelent stay in Chicago with a great breakfast that is include. Awesome location and staff was very helpful."

Reviewed on May 31, 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
$209 nightly
The price is $248 total per night from Jul 2 to Jul 3
$248 total
Jul 2 - Jul 3
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! (2,471 reviews)
"This is the second and the last time I stay at the Palmer. I like the proximity to certain landmarks and the beds were comfy but other than that, the bathroom wasn't clean, there was a lot of hair in the tub, the shower faucet handle was filled with black scum on the inside. There was also a piece ..."

Reviewed on May 31, 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
$220 nightly
The price is $261 total per night from Jun 14 to Jun 15
$261 total
Jun 14 - Jun 15
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! (5,945 reviews)
"It’s a very centric hotel. A great place to start exploring Chicago in any direction. Great pricing, good quality rooms and very helpful staff."

Reviewed on Jun 2, 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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