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, $268 Round Trip

Prices starting at $268 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.

Fri, May 8 - Sun, May 10
RSW
Fort Myers
MDW
Chicago
$268 Roundtrip, found 6 days ago
$268
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Fri, May 8 from Fort Myers to Chicago, returning Sun, May 10, priced at $268 found 6 days ago
Fri, May 8 - Sun, May 10
RSW
Fort Myers
MDW
Chicago
$278 Roundtrip, found 6 days ago
$278
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, May 8 from Fort Myers to Chicago, returning Sun, May 10, priced at $278 found 6 days ago
Fri, May 8 - Sun, May 10
RSW
Fort Myers
MDW
Chicago
$284 Roundtrip, found 6 days ago
$284
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Fri, May 8 from Fort Myers to Chicago, returning Sun, May 10, priced at $284 found 6 days ago
Fri, May 8 - Sun, May 10
RSW
Fort Myers
MDW
Chicago
$288 Roundtrip, found 6 days ago
$288
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, May 8 from Fort Myers to Chicago, returning Sun, May 10, priced at $288 found 6 days ago
Fri, May 8 - Sun, May 10
RSW
Fort Myers
MDW
Chicago
$289 Roundtrip, found 6 days ago
$289
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Fri, May 8 from Fort Myers to Chicago, returning Sun, May 10, priced at $289 found 6 days 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! (1,009 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! (2,059 reviews)
Clean and spacious room, friendly staff. Easy access to concierge through text messaging.

Reviewed on Apr 4, 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
$118 nightly
The price is $139 total per night from Apr 13 to Apr 14
$139 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! (1,946 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! (10,032 reviews)
Very clean

Reviewed on Apr 5, 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 12 to Apr 13
$140 total
Apr 12 - Apr 13
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! (4,059 reviews)
Amazing hotel, felt like a star in my suite! Accessible location and wonderful welcoming staff made this some place I wish we had stayed more than one night.

Reviewed on Apr 5, 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
$135 nightly
The price is $159 total per night from Apr 12 to Apr 13
$159 total
Apr 12 - Apr 13
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! (5,823 reviews)
The room was very clean but the amenities are quite dirty. In general is a big hotel with a lot of movement, many families and a lot of people everywhere, so the breakfast (which is great by the way) is very busy.

Reviewed on Apr 6, 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 26 to Apr 27
$56 total
Apr 26 - Apr 27
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! (1,905 reviews)
The room was clean and staff are friendly.

Reviewed on Apr 5, 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 26 to Apr 27
$106 total
Apr 26 - Apr 27
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! (1,334 reviews)
Everything was great and the staff was super helpful

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 12 to Apr 13
$80 total
Apr 12 - Apr 13
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! (2,932 reviews)
Nice front desk person

Reviewed on Apr 4, 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
$85 nightly
The price is $99 total per night from Apr 12 to Apr 13
$99 total
Apr 12 - Apr 13
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! (2,849 reviews)
Always a great stay when I’m in Chicago. Close to the action and very affordable. There was one afternoon the elevator didn’t go down and I was on the 10th floor so the stairs sucked lol. Other than that I love this place. I crack the window and take in all the big city sounds while I sleep. Thank ...

Reviewed on Apr 5, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$110 nightly
The price is $129 total per night from Apr 7 to Apr 8
$129 total
Apr 7 - Apr 8
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! (2,550 reviews)
On this visit things were ok other than, be told after check in there were issues with the hot water. They gave extra blankets. The staff was very nice and understanding my frustration. Maria n Héctor

Reviewed on Apr 4, 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 26 to Apr 27
$56 total
Apr 26 - Apr 27
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! (1,905 reviews)
The room was clean and staff are friendly.

Reviewed on Apr 5, 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
$137 nightly
The price is $161 total per night from Apr 12 to Apr 13
$161 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! (2,804 reviews)
Staff was friendly, welcoming and helpful. Room was ready promptly and was very clean and comfortable. Breakfast was great, and even though it was very busy during spring break, staff did a great job accommodating the crowd by constantly cleaning tables and refreshing food. My only marks against ...

Reviewed on Apr 5, 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! (2,356 reviews)
The hotel main lobby is so beautiful! The pool was great and warm for the cold weather. Everything is walking distance.

Reviewed on Apr 3, 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
$135 nightly
The price is $159 total per night from Apr 12 to Apr 13
$159 total
Apr 12 - Apr 13
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! (5,823 reviews)
The room was very clean but the amenities are quite dirty. In general is a big hotel with a lot of movement, many families and a lot of people everywhere, so the breakfast (which is great by the way) is very busy.

Reviewed on Apr 6, 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.