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Cheap flights from Sarasota to Chicago from $128

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 6/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Find the cheapest flights from Sarasota to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:15 am - 6:55 am
SRQ
-
MDW
2h 40mnonstop
Southwest Logo
2:10 pm - 5:50 pm
MDW
-
SRQ
2h 40mnonstop
$247Southwest
Thu, Jun 4 - Mon, Jun 8
Southwest Logo
5:15 am - 6:55 am
SRQ
-
MDW
2h 40mnonstop
Southwest Logo
8:20 am - 4:10 pm
MDW
-
SRQ
6h 50m
1 stop
$248Southwest
Thu, Jun 4 - Tue, Jun 9
Allegiant Air Logo
8:32 pm - 8:33 pm
SRQ
-
MDW
25h 01m
1 stop
Allegiant Air Logo
2:47 pm - 5:01 pm
MDW
-
SRQ
25h 14m
1 stop
$249Allegiant Air
Thu, May 21 - Thu, May 28
Delta Logo
3:59 pm - 9:09 pm
SRQ
-
MDW
6h 10m
1 stop
Delta Logo
6:23 am - 11:48 am
MDW
-
SRQ
4h 25m
1 stop
$252Delta
Sat, May 16 - Wed, May 20
Southwest Logo
5:15 am - 6:55 am
SRQ
-
MDW
2h 40mnonstop
Southwest Logo
7:45 am - 3:10 pm
MDW
-
SRQ
6h 25m
2 stops
$253Southwest
Thu, Jun 4 - Tue, Jun 9
Southwest Logo
6:25 am - 1:55 pm
SRQ
-
MDW
8h 30m
2 stops
Southwest Logo
9:50 am - 4:00 pm
MDW
-
SRQ
5h 10m
1 stop
$257Southwest
Sat, May 16 - Tue, May 19
Southwest Logo
6:05 pm - 9:25 pm
SRQ
-
MDW
4h 20m
1 stop
Southwest Logo
7:50 am - 3:30 pm
MDW
-
SRQ
6h 40m
2 stops
$258Southwest
Wed, May 20 - Wed, May 27
Southwest Logo
11:30 am - 4:40 pm
SRQ
-
MDW
6h 10m
1 stop
Southwest Logo
7:50 am - 11:30 am
MDW
-
SRQ
2h 40mnonstop
$259Southwest
Sat, Aug 29 - Sat, Sep 12
Southwest Logo
6:30 pm - 9:55 pm
SRQ
-
MDW
4h 25m
1 stop
Southwest Logo
1:00 pm - 10:00 pm
MDW
-
SRQ
8h 00m
2 stops
$263Southwest
Thu, Jun 4 - Tue, Jun 9
Southwest Logo
7:20 am - 4:05 pm
SRQ
-
MDW
9h 45m
2 stops
Southwest Logo
7:50 am - 11:30 am
MDW
-
SRQ
2h 40mnonstop
$264Southwest
Sat, Aug 29 - Sat, Sep 12

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Southwest flights from Sarasota to Chicago Midway Airport

Our best Southwest deals on Sarasota to Chicago Midway Airport flight tickets
Southwest
Jun 4
SRQ5:15 amSarasota Bradenton Intl
2h 40m
MDW6:55 amChicago Midway
Jun 8
MDW2:10 pmChicago Midway
2h 40m
SRQ5:50 pmSarasota Bradenton Intl
$247
Southwest
Jun 4
SRQ5:15 amSarasota Bradenton Intl
2h 40m
MDW6:55 amChicago Midway
Jun 9
MDW8:20 amChicago Midway
6h 50m
1 stop
SRQ4:10 pmSarasota Bradenton Intl
$248
Southwest
Jun 4
SRQ5:15 amSarasota Bradenton Intl
2h 40m
MDW6:55 amChicago Midway
Jun 9
MDW7:45 amChicago Midway
6h 25m
2 stops
SRQ3:10 pmSarasota Bradenton Intl
$253

Delta flights from Sarasota to Chicago Midway Airport

Our best Delta deals on Sarasota to Chicago Midway Airport flight tickets
Delta
May 16
SRQ3:59 pmSarasota Bradenton Intl
6h 10m
1 stop
MDW9:09 pmChicago Midway
May 20
MDW6:23 amChicago Midway
4h 25m
1 stop
SRQ11:48 amSarasota Bradenton Intl
$252
Delta
Aug 29
SRQ6:00 amSarasota Bradenton Intl
4h 50m
1 stop
MDW9:50 amChicago Midway
Sep 14
MDW6:00 amChicago Midway
5h 35m
1 stop
SRQ12:35 pmSarasota Bradenton Intl
$279
Delta
Jun 20
SRQ6:23 pmSarasota Bradenton Intl
4h 54m
1 stop
MDW10:17 pmChicago Midway
Jun 23
MDW6:00 amChicago Midway
4h 45m
1 stop
SRQ11:45 amSarasota Bradenton Intl
$289

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 April 26, 2026.
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

Cheapest round-trip
Quickest round-trip

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Thu 6/4

5:15 am-6:55 am

Nonstop2h 40m

Chicago Midway

Mon 6/8

2:10 pm-5:50 pm

Nonstop2h 40m

$247

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Thu 6/4

5:15 am-6:55 am

Nonstop2h 40m

Chicago Midway

Tue 6/9

8:20 am-4:10 pm

1 stop6h 50m

$248

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Thu 5/21

8:32 pm-8:33 pm

1 stop25h 01m

Chicago Midway

Thu 5/28

2:47 pm-5:01 pm

1 stop25h 14m

$249

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Sat 5/16

3:59 pm-9:09 pm

1 stop6h 10m

Chicago Midway

Wed 5/20

6:23 am-11:48 am

1 stop4h 25m

$252

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Thu 6/4

5:15 am-6:55 am

Nonstop2h 40m

Chicago Midway

Tue 6/9

7:45 am-3:10 pm

2 stops6h 25m

$253

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Sat 5/16

6:25 am-1:55 pm

2 stops8h 30m

Chicago Midway

Tue 5/19

9:50 am-4:00 pm

1 stop5h 10m

$257

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Wed 5/20

6:05 pm-9:25 pm

1 stop4h 20m

Chicago Midway

Wed 5/27

7:50 am-3:30 pm

2 stops6h 40m

$258

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Sat 8/29

11:30 am-4:40 pm

1 stop6h 10m

Chicago Midway

Sat 9/12

7:50 am-11:30 am

Nonstop2h 40m

$259

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Thu 6/4

6:30 pm-9:55 pm

1 stop4h 25m

Chicago Midway

Tue 6/9

1:00 pm-10:00 pm

2 stops8h 00m

$263

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Sat 8/29

7:20 am-4:05 pm

2 stops9h 45m

Chicago Midway

Sat 9/12

7:50 am-11:30 am

Nonstop2h 40m

$264

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 typical price of a round-trip flight between Sarasota and Chicago Midway Airport?

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

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from Sarasota. The lowest ticket price found for a Tuesday departure recently was $398. 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 $528.

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 in the evening because they tend to be around $556. 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 to Chicago Midway Airport flights?

There is only 1 cabin class available to choose from on Sarasota to Chicago Midway Airport 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?

You could potentially save up to 23% on your flight if you consider stops on a Sarasota to Chicago Midway Airport flight.

How have Sarasota to Chicago Midway Airport flight prices changed over time?

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

$208

Fastest flight time

2h 40m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Sarasota in the past 72 hours is $208. The best round-trip flight deal from Sarasota to Chicago Midway Airport found on momondo in the last 72 hours is $351.
The fastest flight from Sarasota to Chicago Midway Airport takes 2h 40m
Direct flights go from Sarasota to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Sarasota to Chicago Midway Airport

  • 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 40m, 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 $282Free CancellationRating
8.0
4,327 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 $282. Generally, Southwest has 14 flights on this route every week with an average price of $399. 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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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