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

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Cheap Flights from SRQ to MDW starting at $123 One Way, $279 Round Trip

Prices starting at $279 for return flights and $123 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.

Thu, Oct 8 - Mon, Oct 12
SRQ
Sarasota
MDW
Chicago
$279 Roundtrip, found 18 hours ago
$279
Roundtrip
found 18 hours ago
Select Southwest Airlines flight, departing Thu, Oct 8 from Sarasota to Chicago, returning Mon, Oct 12, priced at $279 found 18 hours ago
Sat, Nov 7 - Mon, Nov 9
SRQ
Sarasota
MDW
Chicago
$284 Roundtrip, found 1 day ago
$284
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Nov 7 from Sarasota to Chicago, returning Mon, Nov 9, priced at $284 found 1 day ago
Thu, Oct 8 - Mon, Oct 12
SRQ
Sarasota
MDW
Chicago
$289 Roundtrip, found 18 hours ago
$289
Roundtrip
found 18 hours ago
Select Southwest Airlines flight, departing Thu, Oct 8 from Sarasota to Chicago, returning Mon, Oct 12, priced at $289 found 18 hours ago
Sat, Nov 7 - Mon, Nov 9
SRQ
Sarasota
MDW
Chicago
$294 Roundtrip, found 1 day ago
$294
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Nov 7 from Sarasota to Chicago, returning Mon, Nov 9, priced at $294 found 1 day ago
Thu, Oct 8 - Mon, Oct 12
SRQ
Sarasota
MDW
Chicago
$314 Roundtrip, found 18 hours ago
$314
Roundtrip
found 18 hours ago
Select Southwest Airlines flight, departing Thu, Oct 8 from Sarasota to Chicago, returning Mon, Oct 12, priced at $314 found 18 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
$324 nightly
The price is $385 total per night from Jun 7 to Jun 8
$385 total
Jun 7 - Jun 8
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! (1,093 reviews)
"Staff was nice and helpful"

Reviewed on May 27, 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
$179 nightly
The price is $213 total per night from Jun 28 to Jun 29
$213 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! (2,218 reviews)
"The parking situation was terrible. At check-in, our room was not even ready. Once we finally got into the room, it was very dirty. There was hair in the bed, ashes from smoking, and crumbs all over the carpet. The carpet had clearly not been vacuumed at all."

Reviewed on May 26, 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
$188 nightly
The price is $223 total per night from Jun 3 to Jun 4
$223 total
Jun 3 - Jun 4
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! (10,150 reviews)
"Hotel is pretty "okay" if you are going for business, but our experience was not nice. The Air Conditioner wasn't working on a 65-80 degree outside, I told the front desk if they can help or make a room change but the solution was to give me a floor fan, not the type of help I was hoping and did ..."

Reviewed on May 27, 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
$188 nightly
The price is $223 total per night from Jun 3 to Jun 4
$223 total
Jun 3 - Jun 4
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! (10,150 reviews)
"Hotel is pretty "okay" if you are going for business, but our experience was not nice. The Air Conditioner wasn't working on a 65-80 degree outside, I told the front desk if they can help or make a room change but the solution was to give me a floor fan, not the type of help I was hoping and did ..."

Reviewed on May 27, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
$251 nightly
The price is $298 total per night from Jun 16 to Jun 17
$298 total
Jun 16 - Jun 17
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! (4,270 reviews)
"Location is perfect. And rooftop bar & view is amazing"

Reviewed on May 28, 2026

Hotel Riu Plaza Chicago
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! (1,484 reviews)
"I had travel delays and a situation with my husband and my luggage and they have been very nice about it . Front desk staff is very kind and professional"

Reviewed on May 27, 2026

The Chicago Hotel Collection - Magnificent Mile
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 9 to Jun 10
$73 total
Jun 9 - Jun 10
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
$98 nightly
The price is $108 total per night from Jun 21 to Jun 22
$108 total
Jun 21 - Jun 22
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! (1,448 reviews)
"The front desk people were very unhelpful. I presented them with pictures & videos of rodents in the bed. They said I can reach out to Expedia for a full refund, when I reached out to Expedia they said the hotel only approved of a $24 refund. This is completely ridiculous. I didn’t pay to sleep with ..."

Reviewed on May 27, 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
$104 nightly
The price is $119 total per night from May 31 to Jun 1
$119 total
May 31 - Jun 1
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! (3,018 reviews)
"We choose to stay at this hotel because it is conveniently located near the event we attended. The hotel is not well maintained and everything looks old snd run down. The free breakfast was a plus, but the food was of poor quality. The most surprising thing was the parking fees which were relatively ..."

Reviewed on May 28, 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
$158 nightly
The price is $187 total per night from Jun 3 to Jun 4
$187 total
Jun 3 - Jun 4
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! (3,042 reviews)
"The room was surprisingly clean! I’ve stayed at Hostels before but never this nice! The room was well kept, some aging on the ceiling but nothing to complain about! Staff were extremely friendly and helpful. Will definitely continue to come here when visiting Chicago! 10/10 highly recommend!"

Reviewed on May 27, 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! (2,609 reviews)
"The good: The staff was incredible, friendly and helpful. The location can hardly be beat. The building felt very secure. The bad: no fridge or microwave in the room. And the bathroom was so small that a larger person would have difficulty completing important bodily tasks. (The toilet is so close ..."

Reviewed on May 26, 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 9 to Jun 10
$73 total
Jun 9 - Jun 10
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
$245 nightly
The price is $291 total per night from Jun 28 to Jun 29
$291 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! (2,849 reviews)
"Not much to comment on. Difficult to get to the hotel from parking garage."

Reviewed on May 27, 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
$315 nightly
The price is $375 total per night from Jun 21 to Jun 22
$375 total
Jun 21 - Jun 22
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! (2,465 reviews)
"Great amenities at the hotel. For after hours there is tacos, pizza, dunkin n a 7/11 at the corner open very late. Walking distance to Grant Park. Recommend"

Reviewed on May 28, 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! (5,944 reviews)
"Room dated and not clean, homeless people all over the lobby and breakfast area."

Reviewed on May 27, 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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