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

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Cheap Flights from SRQ to MDW starting at $153 One Way, $339 Round Trip

Prices starting at $339 for return flights and $153 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.

Tue, May 5 - Tue, May 12
SRQ
Sarasota
MDW
Chicago
$339 Roundtrip, found 4 days ago
$339
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, May 5 from Sarasota to Chicago, returning Tue, May 12, priced at $339 found 4 days ago
Wed, May 6 - Tue, May 12
SRQ
Sarasota
MDW
Chicago
$340 Roundtrip, found 4 days ago
$340
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, May 6 from Sarasota to Chicago, returning Tue, May 12, priced at $340 found 4 days ago
Thu, May 7 - Thu, May 14
SRQ
Sarasota
MDW
Chicago
$343 Roundtrip, found 4 days ago
$343
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Thu, May 7 from Sarasota to Chicago, returning Thu, May 14, priced at $343 found 4 days ago
Thu, May 7 - Thu, May 14
SRQ
Sarasota
MDW
Chicago
$349 Roundtrip, found 4 days ago
$349
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Thu, May 7 from Sarasota to Chicago, returning Thu, May 14, priced at $349 found 4 days ago
Thu, May 7 - Tue, May 12
SRQ
Sarasota
MDW
Chicago
$351 Roundtrip, found 4 days ago
$351
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, May 7 from Sarasota to Chicago, returning Tue, May 12, priced at $351 found 4 days ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Hyatt House Chicago West Loop

Hyatt House Chicago West Loop

3.5 out of 5
105 N MAY STREET Chicago IL
$144 nightly
The price is $169 total per night from Feb 5 to Feb 6
$169 total
Feb 5 - Feb 6
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! (1,178 reviews)
Great location. Clean room. Staff were kind and helpful.

Reviewed on Jan 26, 2026

Hyatt House Chicago West Loop
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
$95 nightly
The price is $111 total per night from Feb 1 to Feb 2
$111 total
Feb 1 - Feb 2
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 ...
8.8/10 Excellent! (1,929 reviews)
Room was clean, could use some updates though. Staff were great. Thought it was odd the bar was closed on a Saturday at 5pm

Reviewed on Jan 25, 2026

Crowne Plaza Chicago West Loop by IHG
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
$155 nightly
The price is $182 total per night from Feb 3 to Feb 4
$182 total
Feb 3 - Feb 4
Total with taxes and fees
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (2,583 reviews)
My stay was truly amazing. Thank you and appreciate the hotel hospitality

Reviewed on Jan 25, 2026

Hilton 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.

Hotels In Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is $104 total per night from Jan 31 to Feb 1
$104 total
per night
Jan 31 - Feb 1
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! (9,821 reviews)
Yes perfectly clean

Reviewed on Jan 24, 2026

Congress Plaza 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
The price is $124 total per night from Feb 5 to Feb 6
$124 total
per night
Feb 5 - Feb 6
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 ...
8.4/10 Very Good! (5,583 reviews)
Always a great stay, clean, great breakfast, great pool.

Reviewed on Jan 22, 2026

Embassy Suites by Hilton Chicago Downtown River North
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
The price is $230 total per night from Feb 21 to Feb 22
$230 total
per night
Feb 21 - Feb 22
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 ...
8.2/10 Very Good! (2,195 reviews)
Great stay

Reviewed on Jan 23, 2026

Hilton 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.

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 Jan 29 to Jan 30
$62 total
Jan 29 - Jan 30
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! (1,781 reviews)
The staff is really helpful and informative plus I love the fact that they have a laundry room and vending machines.

Reviewed on Jan 19, 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
$91 nightly
The price is $101 total per night from Jan 28 to Jan 29
$101 total
Jan 28 - Jan 29
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 ...
7.2/10 Good! (1,258 reviews)
Breakfast

Reviewed on Jan 23, 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
$61 nightly
The price is $69 total per night from Feb 1 to Feb 2
$69 total
Feb 1 - Feb 2
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! (2,828 reviews)
The rooftop bar and the fancy breakfast were definitely highlights!

Reviewed on Jan 22, 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
$67 nightly
The price is $79 total per night from Feb 2 to Feb 3
$79 total
Feb 2 - Feb 3
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! (2,717 reviews)
Clean room, comfy bed, hot shower, great cafe and bar. But don’t go when it’s frigid temperatures outside. Even with the space heater, the room was pretty chilly. Otherwise, great!

Reviewed on Jan 19, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$74 nightly
The price is $87 total per night from Feb 22 to Feb 23
$87 total
Feb 22 - Feb 23
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! (2,503 reviews)
Only thing I would change is add mini fridges to the rooms.

Reviewed on Jan 10, 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 Jan 29 to Jan 30
$62 total
Jan 29 - Jan 30
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! (1,781 reviews)
The staff is really helpful and informative plus I love the fact that they have a laundry room and vending machines.

Reviewed on Jan 19, 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
$132 nightly
The price is $155 total per night from Feb 3 to Feb 4
$155 total
Feb 3 - Feb 4
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! (2,820 reviews)
This hotel was extremely family friendly, which was great! However, the waits for the elevators were constantly horrible. The pool was also smaller than the photo made it appear. It was too crowded with kids so we didn't use it. The sound in the rooms was overwhelming because you could hear elevators ...

Reviewed on Jan 24, 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
$159 nightly
The price is $183 total per night from Feb 21 to Feb 22
$183 total
Feb 21 - Feb 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 ...
8.4/10 Very Good! (2,264 reviews)
.

Reviewed on Jan 18, 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
$106 nightly
The price is $124 total per night from Feb 5 to Feb 6
$124 total
Feb 5 - Feb 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 ...
8.4/10 Very Good! (5,583 reviews)
Always a great stay, clean, great breakfast, great pool.

Reviewed on Jan 22, 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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