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Cheap flights from Sarasota to Chicago from $117

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Sarasota to Chicago departing on 2/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Sarasota to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:30 am - 7:15 am
SRQ
-
MDW
2h 45mnonstop
Southwest Logo
1:35 pm - 5:10 pm
MDW
-
SRQ
2h 35mnonstop
$343Southwest
Sat, Jan 17 - Mon, Jan 19
Southwest Logo
5:30 am - 7:15 am
SRQ
-
MDW
2h 45mnonstop
Southwest Logo
12:05 pm - 9:00 pm
MDW
-
SRQ
7h 55m1 stop
$353Southwest
Sat, Jan 17 - Mon, Jan 19
Southwest Logo
12:05 pm - 7:00 pm
SRQ
-
MDW
7h 55m2 stops
Southwest Logo
1:35 pm - 5:10 pm
MDW
-
SRQ
2h 35mnonstop
$358Southwest
Sat, Jan 17 - Mon, Jan 19
Delta Logo
5:20 pm - 10:07 pm
SRQ
-
MDW
5h 47m1 stop
Delta Logo
12:48 pm - 6:10 pm
MDW
-
SRQ
4h 22m1 stop
$363Delta
Sat, Jan 17 - Mon, Jan 19
Southwest Logo
5:40 pm - 7:30 pm
SRQ
-
MDW
2h 50mnonstop
Southwest Logo
1:35 pm - 5:10 pm
MDW
-
SRQ
2h 35mnonstop
$368Southwest
Fri, Jan 16 - Mon, Jan 19
Southwest Logo
8:15 am - 4:55 pm
SRQ
-
MDW
9h 40m2 stops
Southwest Logo
12:30 pm - 8:30 pm
MDW
-
SRQ
7h 00m2 stops
$373Southwest
Sat, Jan 17 - Mon, Jan 19
Southwest Logo
3:45 pm - 7:30 pm
SRQ
-
MDW
4h 45m1 stop
Southwest Logo
1:35 pm - 5:10 pm
MDW
-
SRQ
2h 35mnonstop
$374Southwest
Fri, Jan 16 - Mon, Jan 19
Southwest Logo
8:20 pm - 12:05 am
SRQ
-
MDW
4h 45m1 stop
Southwest Logo
7:40 pm - 11:20 pm
MDW
-
SRQ
2h 40mnonstop
$378Southwest
Thu, Feb 26 - Sun, Mar 1
Southwest Logo
3:45 pm - 7:30 pm
SRQ
-
MDW
4h 45m1 stop
Southwest Logo
9:40 am - 5:00 pm
MDW
-
SRQ
6h 20m1 stop
$383Southwest
Fri, Jan 16 - Mon, Jan 19
Delta Logo
11:08 am - 5:29 pm
SRQ
-
MDW
7h 21m1 stop
Delta Logo
5:00 pm - 4:13 pm
MDW
-
SRQ
22h 13m2 stops
$388Delta
Mon, Feb 2 - Sun, Feb 8

Southwest flights from Sarasota to Chicago Midway Airport

Our best Southwest deals on Sarasota to Chicago Midway Airport flight tickets
Southwest
Jan 17
SRQ5:30 amSarasota Bradenton Intl
2h 45m
MDW7:15 amChicago Midway
Jan 19
MDW1:35 pmChicago Midway
2h 35m
SRQ5:10 pmSarasota Bradenton Intl
$343
Find similar
Southwest
Jan 17
SRQ5:30 amSarasota Bradenton Intl
2h 45m
MDW7:15 amChicago Midway
Jan 19
MDW12:05 pmChicago Midway
7h 55m
1 stop
SRQ9:00 pmSarasota Bradenton Intl
$353
Find similar
Southwest
Jan 17
SRQ12:05 pmSarasota Bradenton Intl
7h 55m
2 stops
MDW7:00 pmChicago Midway
Jan 19
MDW1:35 pmChicago Midway
2h 35m
SRQ5:10 pmSarasota Bradenton Intl
$358
Find similar

Delta flights from Sarasota to Chicago Midway Airport

Our best Delta deals on Sarasota to Chicago Midway Airport flight tickets
Delta
Jan 17
SRQ5:20 pmSarasota Bradenton Intl
5h 47m
1 stop
MDW10:07 pmChicago Midway
Jan 19
MDW12:48 pmChicago Midway
4h 22m
1 stop
SRQ6:10 pmSarasota Bradenton Intl
$363
Find similar
Delta
Feb 2
SRQ11:08 amSarasota Bradenton Intl
7h 21m
1 stop
MDW5:29 pmChicago Midway
Feb 8
MDW5:00 pmChicago Midway
22h 13m
2 stops
SRQ4:13 pmSarasota Bradenton Intl
$388
Find similar
Delta
Feb 2
SRQ5:20 pmSarasota Bradenton Intl
6h 02m
1 stop
MDW10:22 pmChicago Midway
Feb 5
MDW12:48 pmChicago Midway
4h 22m
1 stop
SRQ6:10 pmSarasota Bradenton Intl
$401
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Sarasota to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated December 8, 2025.
Use the filters below to find and compare flights from Sarasota to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Sat 1/17

5:30 am-7:15 am

Nonstop2h 45m

Chicago Midway

Mon 1/19

1:35 pm-5:10 pm

Nonstop2h 35m

$343

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Sat 1/17

5:30 am-7:15 am

Nonstop2h 45m

Chicago Midway

Mon 1/19

12:05 pm-9:00 pm

1 stop7h 55m

$353

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Sat 1/17

12:05 pm-7:00 pm

2 stops7h 55m

Chicago Midway

Mon 1/19

1:35 pm-5:10 pm

Nonstop2h 35m

$358

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Sat 1/17

5:20 pm-10:07 pm

1 stop5h 47m

Chicago Midway

Mon 1/19

12:48 pm-6:10 pm

1 stop4h 22m

$363

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Fri 1/16

5:40 pm-7:30 pm

Nonstop2h 50m

Chicago Midway

Mon 1/19

1:35 pm-5:10 pm

Nonstop2h 35m

$368

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Sat 1/17

8:15 am-4:55 pm

2 stops9h 40m

Chicago Midway

Mon 1/19

12:30 pm-8:30 pm

2 stops7h 00m

$373

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Fri 1/16

3:45 pm-7:30 pm

1 stop4h 45m

Chicago Midway

Mon 1/19

1:35 pm-5:10 pm

Nonstop2h 35m

$374

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Thu 2/26

8:20 pm-12:05 am

1 stop4h 45m

Chicago Midway

Sun 3/1

7:40 pm-11:20 pm

Nonstop2h 40m

$378

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Fri 1/16

3:45 pm-7:30 pm

1 stop4h 45m

Chicago Midway

Mon 1/19

9:40 am-5:00 pm

1 stop6h 20m

$383

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Mon 2/2

11:08 am-5:29 pm

1 stop7h 21m

Chicago Midway

Sun 2/8

5:00 pm-4:13 pm

2 stops22h 13m

$388

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Sarasota to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago Midway Airport?

The month of August is, on average, the cheapest month to fly to Chicago Midway Airport from Sarasota, with most prices found around $310. If you are unable to visit Chicago Midway Airport during the month of August, then departing from Sarasota during the month February is also very affordable. Most momondo users find prices during this month for around $325.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Sarasota. The lowest ticket price found for a Friday departure recently was $373. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Sarasota because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $449.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Sarasota in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $393 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $518. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Sarasota Bradenton Intl to Chicago Midway flight route?

Fly from Sarasota Bradenton Intl to Chicago Midway for the best Sarasota Bradenton Intl - Chicago Midway flight prices

What cabin class options are available on Sarasota Bradenton Intl to Chicago Midway flights?

There is only 1 cabin class available to choose from on Sarasota Bradenton Intl to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Sarasota to Chicago Midway Airport flights?

No. A direct flight is the cheapest option for a flight between Sarasota to Chicago Midway Airport.

When to book flights from Sarasota to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Sarasota to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Sarasota to Chicago Midway Airport (SRQ to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Sarasota to Chicago Midway Airport

Best Price Found

$189

Fastest flight time

2h 45m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Sarasota in the past 72 hours is $189. The best round-trip flight deal from Sarasota to Chicago Midway Airport found on momondo in the last 72 hours is $449.
The fastest flight from Sarasota to Chicago Midway Airport takes 2h 45m
Direct flights go from Sarasota to Chicago Midway Airport every day.
Search flight deals

  • How far is Sarasota Bradenton Intl to Chicago Midway by plane?

    The straight-line distance from Sarasota Bradenton Intl to Chicago Midway is 1040.3 mi. Flights usually cover this in 2h 45m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Sarasota Bradenton Intl Airport to Chicago Midway Airport?

    Prices for flights from Sarasota Bradenton Intl Airport to Chicago Midway Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Sarasota Bradenton Intl Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Sarasota Bradenton Intl Airport to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Sarasota Bradenton Intl Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Sarasota to Chicago Midway Airport?

  • What is the most popular airline from Sarasota to Chicago Midway Airport?

Best airlines flying from Sarasota to Chicago Midway Airport

Compare and see reviews for airlines that fly from Sarasota to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $267Free CancellationRating
8.0
4,254 reviews
Search Southwest flights

  • Southwest Flights From Sarasota to Chicago Midway Airport

    The lowest priced Southwest flight from Sarasota to Chicago Midway Airport from the last 72 hours was $267. Generally, Southwest has 10 flights on this route every week with an average price of $384. Southwest is rated 8.0/10 by our users.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Sarasota to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Sarasota to Chicago for you.

Can I find flights from Sarasota to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Sarasota on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Sarasota to Chicago?

Once all potential Sarasota to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Sarasota to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Sarasota are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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