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

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Cheap Flights from SRQ to MDW starting at $112 One Way, $217 Round Trip

Prices starting at $217 for return flights and $112 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 22 - Tue, Jul 28
SRQ
Sarasota
MDW
Chicago
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Jul 22 from Sarasota to Chicago, returning Tue, Jul 28, priced at $217 found 1 day ago
Wed, Jul 22 - Tue, Jul 28
SRQ
Sarasota
MDW
Chicago
$227 Roundtrip, found 1 day ago
$227
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Jul 22 from Sarasota to Chicago, returning Tue, Jul 28, priced at $227 found 1 day ago
Tue, Aug 4 - Wed, Aug 5
SRQ
Sarasota
MDW
Chicago
$232 Roundtrip, found 17 hours ago
$232
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Tue, Aug 4 from Sarasota to Chicago, returning Wed, Aug 5, priced at $232 found 17 hours ago
Wed, Jul 22 - Tue, Jul 28
SRQ
Sarasota
MDW
Chicago
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jul 22 from Sarasota to Chicago, returning Tue, Jul 28, priced at $237 found 1 day ago
Tue, Aug 4 - Wed, Aug 5
SRQ
Sarasota
MDW
Chicago
$238 Roundtrip, found 17 hours ago
$238
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Tue, Aug 4 from Sarasota to Chicago, returning Wed, Aug 5, priced at $238 found 17 hours ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Hotel Chicago West Loop, SureStay Collection by Best Western

Hotel Chicago West Loop, SureStay Collection by Best Western

2.5 out of 5
1622 W Jackson Blvd Chicago IL
$127 nightly
The price is $151 total per night from Jul 5 to Jul 6
$151 total
Jul 5 - Jul 6
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.2/10 Very Good! (1,111 reviews)
"Our room was very cute and what we expected. They do have a small lot to park so I would recommend getting to the hotel early (you do have to pay for a parking pass). However; upon arrival we were so excited to walk in because it’s decorated so cute. We were immediately hit with an awful sewage smell ..."

Reviewed on Jun 26, 2026

Hotel Chicago West Loop, SureStay Collection by Best Western
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
$234 nightly
The price is $278 total per night from Jul 1 to Jul 2
$278 total
Jul 1 - Jul 2
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! (1,159 reviews)
"Great location! Walking distance to Soldier Field!!!"

Reviewed on Jun 26, 2026

Hyatt Regency McCormick Place Chicago
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
$159 nightly
The price is $190 total per night from Jul 1 to Jul 2
$190 total
Jul 1 - Jul 2
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 ...
8.8/10 Excellent! (1,035 reviews)
"Great hotel. Checked in and staff were friendly. The star of this hotel are the manager Maya!!! She was amazing to speak to and had a warm presence. There was a breakfast attendant we had on our second day that was also very nice but I cant remember her name. Will definitely stay here again as the ..."

Reviewed on Jun 25, 2026

Holiday Inn & Suites Chicago - Downtown by IHG
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
$136 nightly
The price is $162 total per night from Jun 30 to Jul 1
$162 total
Jun 30 - Jul 1
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! (10,133 reviews)
"The hotel is a bit run down, but my room was very clean. The breakfast was good, although it is not included, and for some reason I thought it was. The receptionist was amazing. She was very kind and allowed me to check in early, which I really appreciated. The location is also excellent. I’m giving ..."

Reviewed on Jun 26, 2026

Congress Plaza Hotel
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
$245 nightly
The price is $288 total per night from Jul 18 to Jul 19
$288 total
Jul 18 - Jul 19
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.4/10 Very Good! (2,318 reviews)
"Clean room, staff were very helpful and very friendly. Restaurants and bar were on point. Great experience! Thanks Hilton Chicago O’Hare Airport!"

Reviewed on Jun 25, 2026

Hilton Chicago O'Hare Airport
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
$181 nightly
The price is $215 total per night from Jul 5 to Jul 6
$215 total
Jul 5 - Jul 6
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,827 reviews)
"The staff were very helpful and kind, room clean and a beautiful view. Hotel kept up very well. Our air conditioning worked great on the 23rd floor. Check out, bags held and valet parking plus retrieval very quick and excellent service."

Reviewed on Jun 27, 2026

Omni Chicago 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.

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 Jul 7 to Jul 8
$73 total
Jul 7 - Jul 8
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! (1,965 reviews)
"It was ok for a overnight"

Reviewed on Jun 27, 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
$106 nightly
The price is $117 total per night from Jul 5 to Jul 6
$117 total
Jul 5 - Jul 6
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! (1,539 reviews)
"I rarely leave negative reviews, but this experience was bad enough that I feel obligated to warn other travelers. I booked through Hotels. com because there was no option to book directly with the hotel. The moment we walked in, the lobby was extremely hot, with fans running instead of air conditioning. ..."

Reviewed on Jun 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
$105 nightly
The price is $120 total per night from Jul 5 to Jul 6
$120 total
Jul 5 - Jul 6
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! (3,026 reviews)
"I made good of the stay because it was close to the airport. This hotel is dirty. The carpet is filthy. The room smelled like smoke even though I asked for a smoke free room. The walls were cracking. There is a dollar store behind the hotel, i purchased plug-ins and air freshener for the room. The ..."

Reviewed on Jun 27, 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
$145 nightly
The price is $172 total per night from Jun 30 to Jul 1
$172 total
Jun 30 - Jul 1
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. ...
7.8/10 Good! (3,123 reviews)
"Our stay was great, we had a minor maintenance issue and hotel staff was on it and fixed it immediately. Overall great value for the money."

Reviewed on Jun 26, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$141 nightly
The price is $168 total per night from Jul 8 to Jul 9
$168 total
Jul 8 - Jul 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 ...
7.6/10 Good! (2,635 reviews)
"Perfect location for everything we wanted to do. Walked to the field museum and the theater district. Lots of good restaurants nearby too"

Reviewed on Jun 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 Jul 7 to Jul 8
$73 total
Jul 7 - Jul 8
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! (1,965 reviews)
"It was ok for a overnight"

Reviewed on Jun 27, 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
$212 nightly
The price is $253 total per night from Jul 5 to Jul 6
$253 total
Jul 5 - Jul 6
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! (2,874 reviews)
"The location of the property and the staff were excellent. There was only one elevator working and took a long time to get up or down with everyone trying to use it. The room itself was old, the couch had a big rip and the shower tub had a big stain and the faucet was barely working."

Reviewed on Jun 26, 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
$225 nightly
The price is $268 total per night from Jul 5 to Jul 6
$268 total
Jul 5 - Jul 6
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! (2,497 reviews)
"Location, history, staff"

Reviewed on Jun 27, 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
$163 nightly
The price is $194 total per night from Jul 5 to Jul 6
$194 total
Jul 5 - Jul 6
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! (5,983 reviews)
"Close to central area and Michigan avenue"

Reviewed on Jun 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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