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

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Cheap Flights from SRQ to MDW starting at $114 One Way, $222 Round Trip

Prices starting at $222 for return flights and $114 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.

Sat, Aug 22 - Tue, Aug 25
SRQ
Sarasota
MDW
Chicago
$222 Roundtrip, found 6 days ago
$222
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Aug 22 from Sarasota to Chicago, returning Tue, Aug 25, priced at $222 found 6 days ago
Sat, Aug 22 - Tue, Aug 25
SRQ
Sarasota
MDW
Chicago
$232 Roundtrip, found 6 days ago
$232
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Aug 22 from Sarasota to Chicago, returning Tue, Aug 25, priced at $232 found 6 days ago
Sat, Aug 22 - Tue, Aug 25
SRQ
Sarasota
MDW
Chicago
$238 Roundtrip, found 6 days ago
$238
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Aug 22 from Sarasota to Chicago, returning Tue, Aug 25, priced at $238 found 6 days ago
Tue, Aug 11 - Mon, Aug 17
SRQ
Sarasota
MDW
Chicago
$244 Roundtrip, found 6 days ago
$244
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Aug 11 from Sarasota to Chicago, returning Mon, Aug 17, priced at $244 found 6 days ago
Sat, Aug 22 - Tue, Aug 25
SRQ
Sarasota
MDW
Chicago
$248 Roundtrip, found 6 days ago
$248
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Aug 22 from Sarasota to Chicago, returning Tue, Aug 25, priced at $248 found 6 days 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
$151 nightly
The price is $180 total per night from Jul 12 to Jul 13
$180 total
Jul 12 - Jul 13
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! (1,123 reviews)
"The room was small but clean. The bed seemed smaller than a double but wasn't a big deal. The staff were very friendly and helpful. I was there to go to the University of Chicago hospital, which was very close by. The hotel parking is $25, however I parked in the lot next door for $11 all night."

Reviewed on Jul 9, 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
$262 nightly
The price is $311 total per night from Aug 9 to Aug 10
$311 total
Aug 9 - Aug 10
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! (1,190 reviews)
"It was a pleasure staying at this property. I will return in the future God willing"

Reviewed on Jul 6, 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
$184 nightly
The price is $219 total per night from Aug 9 to Aug 10
$219 total
Aug 9 - Aug 10
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! (1,063 reviews)
"Everything was great. This was an overnight stay and this property exceeded my expectations."

Reviewed on Jul 8, 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

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
$243 nightly
The price is $289 total per night from Aug 9 to Aug 10
$289 total
Aug 9 - Aug 10
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! (1,893 reviews)
"Our stay was fantastic and we will be back! Great location, the restaurant was delicious and the rooms were setup great for our family of 6"

Reviewed on Jul 9, 2026

Omni Chicago Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
$154 nightly
The price is $183 total per night from Jul 27 to Jul 28
$183 total
Jul 27 - Jul 28
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
The Chicago Hotel Collection Ambassador Gold Coast
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$206 nightly
The price is $245 total per night from Aug 6 to Aug 7
$245 total
Aug 6 - Aug 7
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! (10,217 reviews)
"Our stay was great, best was comfortable and room was clean."

Reviewed on Jul 9, 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.

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 Aug 3 to Aug 4
$73 total
Aug 3 - Aug 4
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! (1,977 reviews)
"All the machines out off the Service."

Reviewed on Jul 8, 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
$115 nightly
The price is $127 total per night from Jul 21 to Jul 22
$127 total
Jul 21 - Jul 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! (1,570 reviews)
"The outside looked nice but had trash everywhere from a group of day workers staying there. They would smoke and eat near the entrance with their trash laying around There was remodeling supplies in the halls. The hotel was in need of several major repairs. The pool and hot tub were too hot and nasty. ..."

Reviewed on Jul 9, 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
$109 nightly
The price is $125 total per night from Jul 19 to Jul 20
$125 total
Jul 19 - Jul 20
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! (3,059 reviews)
"This hotel was the most run down place I’ve ever been to. The room was as gross. The carpet was severely stained. The walls and ceiling had patch work done. It smelled and was awful. On top of this you have the nerve to charge a $100 incidental fee. I’m very disappointed in Choice. I’ll never ever ..."

Reviewed on Jul 9, 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
$157 nightly
The price is $187 total per night from Jul 28 to Jul 29
$187 total
Jul 28 - Jul 29
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! (3,167 reviews)
"Moldy private equity owned bummer."

Reviewed on Jul 9, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$163 nightly
The price is $194 total per night from Aug 9 to Aug 10
$194 total
Aug 9 - Aug 10
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! (2,685 reviews)
"Older hotel and noisily placed in the South Loop, but perfectly fine for a two-star accommodation. I would have preferred updated charging stations in the room. Otherwise it was fine."

Reviewed on Jul 9, 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 Aug 3 to Aug 4
$73 total
Aug 3 - Aug 4
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! (1,977 reviews)
"All the machines out off the Service."

Reviewed on Jul 8, 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
$263 nightly
The price is $313 total per night from Jul 19 to Jul 20
$313 total
Jul 19 - Jul 20
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! (2,911 reviews)
"The property was decently maintained. The lobby and dinning area were clean and inviting. The pool was small but clean with enough towels available for all guests. The breakfast was fresh and had enough options for both adults and kids. The room was clean and the bedding smelled fresh. The bathroom ..."

Reviewed on Jul 9, 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
$241 nightly
The price is $287 total per night from Aug 9 to Aug 10
$287 total
Aug 9 - Aug 10
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! (2,511 reviews)
"This is a very old hotel. Very well kept. Beautiful. Lots of history. So many celebs performed in the Empire Room. They have a very large lobby bar. Kind staff. Nearby restaurants all around. Location is easy to get around town 18 min walk to anything."

Reviewed on Jul 9, 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
$192 nightly
The price is $228 total per night from Jul 19 to Jul 20
$228 total
Jul 19 - Jul 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! (6,022 reviews)
"Had a really nice stay for the 4th of July weekend. Breakfast was great and the rooms were very spacious. Only complaint was the room did not stock any bath towels when we checked in."

Reviewed on Jul 9, 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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