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

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Cheap Flights from SRQ to MDW starting at $116 One Way, $247 Round Trip

Prices starting at $247 for return flights and $116 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, May 7 - Thu, May 14
SRQ
Sarasota
MDW
Chicago
$247 Roundtrip, found 2 days ago
$247
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, May 7 from Sarasota to Chicago, returning Thu, May 14, priced at $247 found 2 days ago
Thu, May 7 - Thu, May 14
SRQ
Sarasota
MDW
Chicago
$257 Roundtrip, found 2 days ago
$257
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, May 7 from Sarasota to Chicago, returning Thu, May 14, priced at $257 found 2 days ago
Thu, May 7 - Thu, May 14
SRQ
Sarasota
MDW
Chicago
$262 Roundtrip, found 2 days ago
$262
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, May 7 from Sarasota to Chicago, returning Thu, May 14, priced at $262 found 2 days ago
Thu, May 7 - Thu, May 14
SRQ
Sarasota
MDW
Chicago
$293 Roundtrip, found 2 days ago
$293
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, May 7 from Sarasota to Chicago, returning Thu, May 14, priced at $293 found 2 days ago
Thu, May 7 - Thu, May 14
SRQ
Sarasota
MDW
Chicago
$297 Roundtrip, found 2 days ago
$297
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, May 7 from Sarasota to Chicago, returning Thu, May 14, priced at $297 found 2 days ago

Hotel Ideas near Midway Intl.

Airport Hotels near Midway Intl.

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
$103 nightly
The price is $121 total per night from Apr 1 to Apr 2
$121 total
Apr 1 - Apr 2
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! (9,968 reviews)
Nice room, a bit disturbed I had to pay a safety fee of$25.00 for each day of my stay.

Reviewed on Mar 20, 2026

Congress Plaza Hotel
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
506 West Harrison Street Chicago IL
$120 nightly
The price is $141 total per night from Mar 22 to Mar 23
$141 total
Mar 22 - Mar 23
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! (1,002 reviews)
Nice location for bus travelers and connection by metro

Reviewed on Mar 18, 2026

Holiday Inn & Suites Chicago - Downtown by IHG
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
$125 nightly
The price is $147 total per night from Mar 29 to Mar 30
$147 total
Mar 29 - Mar 30
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! (2,014 reviews)
Water in restrooms wasn’t working. Staff rude when we got checking in. Room wasn’t getting warm

Reviewed on Mar 16, 2026

Crowne Plaza Chicago West Loop 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
$103 nightly
The price is $121 total per night from Apr 1 to Apr 2
$121 total
Apr 1 - Apr 2
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! (9,968 reviews)
Nice room, a bit disturbed I had to pay a safety fee of$25.00 for each day of my stay.

Reviewed on Mar 20, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
$156 nightly
The price is $183 total per night from Apr 6 to Apr 7
$183 total
Apr 6 - Apr 7
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! (3,569 reviews)
Staff was friendly, rooms were clean and breakfast was delicious

Reviewed on Mar 19, 2026

Hotel Riu Plaza Chicago
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
$130 nightly
The price is $153 total per night from Mar 29 to Mar 30
$153 total
Mar 29 - Mar 30
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! (5,749 reviews)
The location was great, near plenty of restaurants and shopping. The room was a great layout plenty of space.

Reviewed on Mar 19, 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.

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 Mar 25 to Mar 26
$62 total
Mar 25 - Mar 26
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! (1,876 reviews)
Staff can Sametimes be very rude. I stayed at Motel 6 in Bridgeview IL and got to stay 3 months now you can only stay 14 days before having to leave and wait 72 hours before you can come back. It's really different now especially when you are homeless.

Reviewed on Mar 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
$96 nightly
The price is $107 total per night from Apr 5 to Apr 6
$107 total
Apr 5 - Apr 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 ...
7.4/10 Good! (1,306 reviews)
Clean room, nice staff

Reviewed on Mar 19, 2026

Country Inn & Suites by Radisson, Chicago O'Hare South, IL
O'Hare Inn & Suites

O'Hare Inn & Suites

2 out of 5
4101 Mannheim Rd Schiller Park IL
$64 nightly
The price is $72 total per night from Mar 24 to Mar 25
$72 total
Mar 24 - Mar 25
Total with taxes and fees
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Allstate Arena and Fashion ...
5.8/10 (1,000 reviews)
Literally the worst place! We showed up at 11PM and they had cancelled our room without telling us. Manager did not want to help and we were stuck without a hotel room for the night. STAY AWAY!

Reviewed on Mar 19, 2026

O'Hare Inn & Suites
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
The price is $94 total per night from Mar 24 to Mar 25
$94 total
per night
Mar 24 - Mar 25
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! (2,812 reviews)
Great experience

Reviewed on Mar 19, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
The price is $121 total per night from Mar 29 to Mar 30
$121 total
per night
Mar 29 - Mar 30
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! (2,525 reviews)
It’s was good for a last minute stay. Nothing special, nothing bad.

Reviewed on Mar 17, 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
The price is $62 total per night from Mar 25 to Mar 26
$62 total
per night
Mar 25 - Mar 26
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! (1,876 reviews)
Staff can Sametimes be very rude. I stayed at Motel 6 in Bridgeview IL and got to stay 3 months now you can only stay 14 days before having to leave and wait 72 hours before you can come back. It's really different now especially when you are homeless.

Reviewed on Mar 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
$144 nightly
The price is $169 total per night from Apr 6 to Apr 7
$169 total
Apr 6 - Apr 7
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! (2,794 reviews)
Very accommodating, in a safe and fun part of chicago.

Reviewed on Mar 19, 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 Apr 5 to Apr 6
$183 total
Apr 5 - Apr 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! (2,326 reviews)
Beautiful property, great resturant on site, an the pool and spa was amazing.

Reviewed on Mar 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
$130 nightly
The price is $153 total per night from Mar 29 to Mar 30
$153 total
Mar 29 - Mar 30
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! (5,749 reviews)
The location was great, near plenty of restaurants and shopping. The room was a great layout plenty of space.

Reviewed on Mar 19, 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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