Cheap flights from RSW to MDW (Southwest Florida Intl. to Midway Intl.)

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Cheap Flights from RSW to MDW starting at $143 One Way, $293 Round Trip

Prices starting at $293 for return flights and $143 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, Jul 1 - Tue, Jul 7
RSW
Fort Myers
MDW
Chicago
$293 Roundtrip, found 9 hours ago
$293
Roundtrip
found 9 hours ago
Select Southwest Airlines flight, departing Wed, Jul 1 from Fort Myers to Chicago, returning Tue, Jul 7, priced at $293 found 9 hours ago
Thu, Jul 2 - Tue, Jul 7
RSW
Fort Myers
MDW
Chicago
$295 Roundtrip, found 6 hours ago
$295
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Thu, Jul 2 from Fort Myers to Chicago, returning Tue, Jul 7, priced at $295 found 6 hours ago
Tue, May 19 - Tue, May 26
RSW
Fort Myers
MDW
Chicago
$297 Roundtrip, found 4 days ago
$297
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, May 19 from Fort Myers to Chicago, returning Tue, May 26, priced at $297 found 4 days ago
Sat, May 9 - Wed, May 13
RSW
Fort Myers
MDW
Chicago
$299 Roundtrip, found 1 day ago
$299
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, May 9 from Fort Myers to Chicago, returning Wed, May 13, priced at $299 found 1 day ago
Thu, May 14 - Mon, May 18
RSW
Fort Myers
MDW
Chicago
$301 Roundtrip, found 2 hours ago
$301
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Thu, May 14 from Fort Myers to Chicago, returning Mon, May 18, priced at $301 found 2 hours ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
$128 nightly
The price is $151 total per night from Apr 12 to Apr 13
$151 total
Apr 12 - Apr 13
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 ...
8.6/10 Excellent! (1,011 reviews)
.

Reviewed on Apr 4, 2026

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
$135 nightly
The price is $158 total per night from Apr 26 to Apr 27
$158 total
Apr 26 - Apr 27
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! (2,066 reviews)
All the employees were stuck up, rude to say the least, and not very compassionate let alone understanding Life on life's terms. I don't care but I will never a room from this hotel ever again. Hell I will never rent another hotel room from this flight out company again. Really they're making me ...

Reviewed on Apr 6, 2026

Crowne Plaza Chicago West Loop by IHG
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
55 E 11th Street Chicago IL
$122 nightly
The price is $143 total per night from Apr 13 to Apr 14
$143 total
Apr 13 - Apr 14
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
8.8/10 Excellent! (1,949 reviews)
Staff and service was great. I’ve stayed here every year since 2020 and I love it.

Reviewed on Apr 5, 2026

Hilton Garden Inn Chicago Downtown South Loop
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
$110 nightly
The price is $129 total per night from Apr 16 to Apr 17
$129 total
Apr 16 - Apr 17
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! (10,052 reviews)
Air conditioner was really noisy, they told me there is a free parking when i booked, no towel in the bathroom

Reviewed on Apr 6, 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
$119 nightly
The price is $140 total per night from Apr 26 to Apr 27
$140 total
Apr 26 - Apr 27
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
9/10 Wonderful! (4,076 reviews)
No hot water

Reviewed on Apr 6, 2026

Hilton Chicago/Magnificent Mile Suites
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
$139 nightly
The price is $163 total per night from Apr 19 to Apr 20
$163 total
Apr 19 - Apr 20
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! (5,833 reviews)
Should probably clean the carpet! Staff was polite once dirty floor was brought to their attention, but only after i threatened a bad review smh!

Reviewed on Apr 7, 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.

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
$50 nightly
The price is $56 total per night from Apr 29 to Apr 30
$56 total
Apr 29 - Apr 30
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! (1,909 reviews)
It was good near the airport easy to get

Reviewed on Apr 6, 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
$95 nightly
The price is $106 total per night from Apr 27 to Apr 28
$106 total
Apr 27 - Apr 28
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 ...
7.4/10 Good! (1,335 reviews)
Hot tub and pool has a funky smell and they are cloudy but we’re both warm!

Reviewed on Apr 6, 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
$70 nightly
The price is $80 total per night from Apr 13 to Apr 14
$80 total
Apr 13 - Apr 14
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 ...
8/10 Very Good! (2,941 reviews)
Shuttle was fast, rooms clean and quiet. Nice breakfast. Purchased last minute and was a great option.

Reviewed on Apr 6, 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
$77 nightly
The price is $90 total per night from Apr 14 to Apr 15
$90 total
Apr 14 - Apr 15
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! (2,852 reviews)
Clean room

Reviewed on Apr 6, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$101 nightly
The price is $119 total per night from Apr 8 to Apr 9
$119 total
Apr 8 - Apr 9
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! (2,554 reviews)
This Travel Lodge is in a prime location just off of Roosevelt park and convenient to public transportation. The building is old and the rooms are dated with rad heat.

Reviewed on Apr 6, 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
$50 nightly
The price is $56 total per night from Apr 29 to Apr 30
$56 total
Apr 29 - Apr 30
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! (1,909 reviews)
It was good near the airport easy to get

Reviewed on Apr 6, 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
$153 nightly
The price is $179 total per night from Apr 12 to Apr 13
$179 total
Apr 12 - Apr 13
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! (2,807 reviews)
The bathroom had clear water damage on doors and walls with no fan. Wallpaper was peeling off. Half of the elevators were closed. Check in was at 4 pm and a super slow line with only one worker who took 10 minutes per new guest. People seemed to be partying late even on a weeknight. I regret not ...

Reviewed on Apr 6, 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 $241 total per night from Apr 26 to Apr 27
$241 total
Apr 26 - Apr 27
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! (2,362 reviews)
Second time staying here for a business event. Great Property and location. Clean rooms and housekeeping was so nice when walking in the halls. Starbucks is a bonus on-site.

Reviewed on Apr 6, 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
$139 nightly
The price is $163 total per night from Apr 19 to Apr 20
$163 total
Apr 19 - Apr 20
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! (5,833 reviews)
Should probably clean the carpet! Staff was polite once dirty floor was brought to their attention, but only after i threatened a bad review smh!

Reviewed on Apr 7, 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.

RSW 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 Southwest Florida Intl. Airport (RSW) to Midway Intl. Airport (MDW)?
Listen up. We're about to make your upcoming vacation even more exciting. Southwest Airlines flies directly from Southwest Florida Intl. Airport to Midway Airport, so you'll be hitting the tarmac and starting your next big adventure before you know it.
What is the shortest flight from Southwest Florida Intl. Airport to Chicago Airport?
If you think your vacation hours should be spent 'vacationing' instead of flying, you'll enjoy the journey from RSW to MDW. It's a wonderfully short 2 hours and 55 minutes.
How many hours flight from Southwest Florida Intl. Airport to Midway Airport?
From Southwest Florida Intl. Airport (RSW) to Chicago Airport, you'll be in your seat for around 3 hours and 1 minute. Get comfy, order a glass of wine and take out your noise-canceling earphones. It's time to rewatch your favorite TV shows.
What airlines have the most flights from Southwest Florida Intl. Airport (RSW) to Chicago Airport?
Whether you pick window or aisle, you'll fly to your destination easily and comfortably with Southwest Airlines. This quality air carrier has 115 flights from Southwest Florida Intl. Airport to Midway Intl. Airport (MDW) per month.

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.