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 15 - Wed, Jul 22
SRQ
Sarasota
MDW
Chicago
$217 Roundtrip, found 3 days ago
$217
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Jul 15 from Sarasota to Chicago, returning Wed, Jul 22, priced at $217 found 3 days ago
Wed, Jul 15 - Wed, Jul 22
SRQ
Sarasota
MDW
Chicago
$227 Roundtrip, found 3 days ago
$227
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Jul 15 from Sarasota to Chicago, returning Wed, Jul 22, priced at $227 found 3 days ago
Tue, Aug 4 - Wed, Aug 5
SRQ
Sarasota
MDW
Chicago
$232 Roundtrip, found 2 days ago
$232
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Aug 4 from Sarasota to Chicago, returning Wed, Aug 5, priced at $232 found 2 days ago
Wed, Jul 22 - Tue, Jul 28
SRQ
Sarasota
MDW
Chicago
$237 Roundtrip, found 4 days ago
$237
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Jul 22 from Sarasota to Chicago, returning Tue, Jul 28, priced at $237 found 4 days ago
Tue, Aug 4 - Wed, Aug 5
SRQ
Sarasota
MDW
Chicago
$238 Roundtrip, found 2 days ago
$238
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Aug 4 from Sarasota to Chicago, returning Wed, Aug 5, priced at $238 found 2 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
$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! (1,104 reviews)
"A nice surprise! Enjoyed our stay. We will be back!"

Reviewed on Jun 21, 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
$228 nightly
The price is $271 total per night from Jul 8 to Jul 9
$271 total
Jul 8 - Jul 9
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! (1,141 reviews)
"So I had gotten free parking with my room which wasn’t free at all the Hotel says it’s free but the parking garage says otherwise pretty much the parking attendance give you a hard time with no help and your forced to pay to leave only complaint I had about it the hotel."

Reviewed on Jun 21, 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! (1,039 reviews)
"Way overpriced for what you get."

Reviewed on Jun 21, 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 29 to Jun 30
$162 total
Jun 29 - Jun 30
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! (10,155 reviews)
"Room was super clean. Comfortable bed. Shower took quite awhile to warm up. Overall great location and will stay again."

Reviewed on Jun 22, 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
$139 nightly
The price is $166 total per night from Jul 1 to Jul 2
$166 total
Jul 1 - Jul 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
9/10 Wonderful! (4,455 reviews)
"Cleaneage rooms. Great location. Lovely staff"

Reviewed on Jun 21, 2026

Hilton Chicago/Magnificent Mile Suites
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
$135 nightly
The price is $154 total per night from Jun 28 to Jun 29
$154 total
Jun 28 - Jun 29
Total with taxes and fees
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,703 reviews)
"Amazing hotel! We will be back"

Reviewed on Jun 22, 2026

Hyatt Regency O'Hare 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.

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! (1,961 reviews)
"Nice spot ! Bonne accessibilité"

Reviewed on Jun 21, 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 Jun 29 to Jun 30
$127 total
Jun 29 - Jun 30
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 ...
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
$100 nightly
The price is $115 total per night from Jun 28 to Jun 29
$115 total
Jun 28 - Jun 29
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! (3,025 reviews)
"not bad, but not amazing! price was fair!"

Reviewed on Jun 21, 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 Jul 5 to Jul 6
$172 total
Jul 5 - Jul 6
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! (3,112 reviews)
"Easy check in, clean room, helpful staff, great location."

Reviewed on Jun 22, 2026

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
$122 nightly
The price is $146 total per night from Jul 5 to Jul 6
$146 total
Jul 5 - Jul 6
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! (2,633 reviews)
"Basic but a great location"

Reviewed on Jun 22, 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! (1,961 reviews)
"Nice spot ! Bonne accessibilité"

Reviewed on Jun 21, 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
$226 nightly
The price is $269 total per night from Jun 28 to Jun 29
$269 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! (2,876 reviews)
"It was a nice place if you want to be closer to downtown, otherwise I would suggest staying closer to the place where you’re going to be, because transportation is a bit complicated and expensive"

Reviewed on Jun 20, 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
$209 nightly
The price is $248 total per night from Jun 30 to Jul 1
$248 total
Jun 30 - Jul 1
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! (2,494 reviews)
"Prepaid parking through Expedia not honored at the hotel. Staff completely unhelpful in sorting this issue out. Forced to double pay for parking. Rooms dated with older furnishings. Beds old. Plumbing drained poorly. Location nice but otherwise I would not recommend."

Reviewed on Jun 22, 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
$147 nightly
The price is $175 total per night from Jul 5 to Jul 6
$175 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! (5,991 reviews)
"Breakfast and manager happy hour were very crowded"

Reviewed on Jun 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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