Cheap flights from SRQ to MDW (Sarasota-Bradenton Intl. to Midway Intl.)

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Cheap Flights from SRQ to MDW starting at $119 One Way, $248 Round Trip

Prices starting at $248 for return flights and $119 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.

Mon, Jun 8 - Tue, Jun 16
SRQ
Sarasota
MDW
Chicago
$248 Roundtrip, found 14 hours ago
$248
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Mon, Jun 8 from Sarasota to Chicago, returning Tue, Jun 16, priced at $248 found 14 hours ago
Mon, Jun 8 - Tue, Jun 16
SRQ
Sarasota
MDW
Chicago
$258 Roundtrip, found 14 hours ago
$258
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Mon, Jun 8 from Sarasota to Chicago, returning Tue, Jun 16, priced at $258 found 14 hours ago
Mon, Jun 8 - Tue, Jun 16
SRQ
Sarasota
MDW
Chicago
$263 Roundtrip, found 14 hours ago
$263
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Mon, Jun 8 from Sarasota to Chicago, returning Tue, Jun 16, priced at $263 found 14 hours ago
Mon, Jun 8 - Tue, Jun 16
SRQ
Sarasota
MDW
Chicago
$284 Roundtrip, found 14 hours ago
$284
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Mon, Jun 8 from Sarasota to Chicago, returning Tue, Jun 16, priced at $284 found 14 hours ago
Mon, Jun 8 - Tue, Jun 16
SRQ
Sarasota
MDW
Chicago
$284 Roundtrip, found 14 hours ago
$284
Roundtrip
found 14 hours ago
Select Delta flight, departing Mon, Jun 8 from Sarasota to Chicago, returning Tue, Jun 16, priced at $284 found 14 hours ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

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
$145 nightly
The price is $172 total per night from May 10 to May 11
$172 total
May 10 - May 11
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! (2,146 reviews)
The view from the balcony everything was great

Reviewed on May 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
$126 nightly
The price is $150 total per night from May 26 to May 27
$150 total
May 26 - May 27
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! (1,982 reviews)
Clean room, friendly staff, fast elevator. We would stay here again. Actually, we might prefer to stay at the adjacent hotel run by the same company, (lower room rates and free breakfast are included at that hotel).

Reviewed on May 3, 2026

Hilton Garden Inn Chicago Downtown South Loop
Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

3 out of 5
59 E. 11th Street Chicago IL
$143 nightly
The price is $170 total per night from May 25 to May 26
$170 total
May 25 - May 26
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
8.8/10 Excellent! (2,316 reviews)
Good breakfast!

Reviewed on May 5, 2026

Homewood Suites by Hilton 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

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
$125 nightly
The price is $148 total per night from May 25 to May 26
$148 total
May 25 - May 26
Total with taxes and fees
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
8.2/10 Very Good! (2,679 reviews)
The hotel Felix was perfect . Walking distance to everything I wanted to do . Friendly staff and great accommodations.

Reviewed on May 5, 2026

Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$144 nightly
The price is $171 total per night from May 26 to May 27
$171 total
May 26 - May 27
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (5,162 reviews)
Really nice rooms, and the staff was amazing!

Reviewed on May 5, 2026

River Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
$151 nightly
The price is $180 total per night from May 27 to May 28
$180 total
May 27 - May 28
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! (4,058 reviews)
Beautiful and clean. Staff was very friendly and accommodating, The roof top bar was sunning!!

Reviewed on May 5, 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
$55 nightly
The price is $62 total per night from May 19 to May 20
$62 total
May 19 - May 20
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! (1,937 reviews)
This properry was satisfactory for my purposes. One late night there was a very noisy neighbor. Also, i contactrd expedia to modify my reservation by changing the name on the reservation. I did it on a chat with an automated agent. The change was easily made but the hotel wasn't notified. The desk ...

Reviewed on May 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
$96 nightly
The price is $106 total per night from May 27 to May 28
$106 total
May 27 - May 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! (1,395 reviews)
Best salsa at the breakfast. This place is exactly what we needed for a night stay. Staff very helpful and kind. Rooms clean and comfortable!

Reviewed on May 5, 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
$94 nightly
The price is $108 total per night from May 25 to May 26
$108 total
May 25 - May 26
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! (2,996 reviews)
The hotel was definitely old and outdated but was extremely clean. The staff was super friendly and the free shuttle to and from the airport was a nice perk. The shuttle drivers were friendly and helpful. The room was very clean and the beds were comfortable enough for a good sleep after a long international ...

Reviewed on May 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
$101 nightly
The price is $120 total per night from May 25 to May 26
$120 total
May 25 - May 26
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! (2,948 reviews)
Great central location, lots to do nearby.

Reviewed on May 4, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$105 nightly
The price is $125 total per night from May 27 to May 28
$125 total
May 27 - May 28
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! (2,578 reviews)
You get what you pay for. So, here, you don't pay much. When we stayed it was lowest cost in the whole area. For that you get a clean bed, clean bath and very plain, old, building. We were comfortable and felt safe. Staff was fantastic.

Reviewed on May 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
$55 nightly
The price is $62 total per night from May 19 to May 20
$62 total
May 19 - May 20
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! (1,937 reviews)
This properry was satisfactory for my purposes. One late night there was a very noisy neighbor. Also, i contactrd expedia to modify my reservation by changing the name on the reservation. I did it on a chat with an automated agent. The change was easily made but the hotel wasn't notified. The desk ...

Reviewed on May 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
$176 nightly
The price is $209 total per night from May 25 to May 26
$209 total
May 25 - May 26
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! (2,845 reviews)
I had a pleasant stay overall at Embassy Suites. The breakfast was excellent, and the service throughout the hotel was consistently good. The staff were friendly, professional, and helpful during our visit. The main issue we encountered was with the elevators. Although there are four elevators in ...

Reviewed on May 4, 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
$172 nightly
The price is $199 total per night from May 25 to May 26
$199 total
May 25 - May 26
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! (2,429 reviews)
Beautiful hotel, staff friendly. Expensive

Reviewed on May 4, 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
$144 nightly
The price is $171 total per night from May 25 to May 26
$171 total
May 25 - May 26
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! (5,927 reviews)
Clean room, friendly staff, hot breakfast with a lot of options, excellent valet parking

Reviewed on May 5, 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.

SRQ to MDW Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date
SRQ Address & GPS
Address:
6000 Airport Circle
Sarasota FL, 34243
United States
IATA Code:
SRQ
Longitude:
-82.553282
Latitude:
27.38748
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 Sarasota-Bradenton Intl. Airport (SRQ) to Midway Intl. Airport (MDW)?
You won't have to concern yourself with changing planes or missing your connection on this route. Southwest Airlines will fly you straight from SRQ Airport to Chicago Airport.
What is the shortest flight from Sarasota-Bradenton Intl. Airport (SRQ) to Chicago Airport?
From Sarasota, the wonderful sights and sounds of Chicago are 4 hours and 8 minutes away. Lock in your favorite seat, or perhaps even upgrade to one with a bit more legroom, and jet to your destination in pure comfort.
How many hours flight from SRQ Airport to Midway Airport?
On average, the flight from SRQ to Midway Airport takes 4 hours and 13 minutes. If you're looking to be as comfortable as you can, contemplate upgrading your seat using miles or cash.
What airlines have the most flights from SRQ to Chicago Airport?
With 67 flights every month between Sarasota and Chicago, Southwest Airlines will get you there comfortably and safely.

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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