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Cheap flights from Sarasota to Chicago from $108

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 10/27. 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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Cheap round-trip flights

Southwest Logo
3:55 pm - 5:40 pmSRQ-MDW
2h 45mnonstop
Southwest Logo
5:25 am - 11:45 amMDW-SRQ
5h 20m1 stop
$307Southwest
Find Deal
Wed, Oct 15 - Wed, Oct 22
Delta Logo
6:00 am - 11:52 amSRQ-MDW
6h 52m1 stop
Delta Logo
7:02 pm - 2:09 pmMDW-SRQ
18h 07m1 stop
$311Delta
Find Deal
Wed, Nov 12 - Mon, Nov 17
Southwest Logo
3:55 pm - 5:40 pmSRQ-MDW
2h 45mnonstop
Southwest Logo
12:35 pm - 9:55 pmMDW-SRQ
8h 20m2 stops
$312Southwest
Find Deal
Wed, Oct 15 - Wed, Oct 22
Southwest Logo
3:55 pm - 5:40 pmSRQ-MDW
2h 45mnonstop
Southwest Logo
11:45 am - 8:00 pmMDW-SRQ
7h 15m1 stop
$315Southwest
Find Deal
Wed, Oct 15 - Sat, Oct 18
Southwest Logo
3:35 pm - 5:20 pmSRQ-MDW
2h 45mnonstop
Southwest Logo
1:40 pm - 5:10 pmMDW-SRQ
2h 30mnonstop
$317Southwest
Find Deal
Fri, Oct 17 - Tue, Oct 21
Southwest Logo
3:55 pm - 5:40 pmSRQ-MDW
2h 45mnonstop
Southwest Logo
12:50 pm - 9:30 pmMDW-SRQ
7h 40m2 stops
$320Southwest
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Wed, Oct 15 - Sat, Oct 18
Southwest Logo
7:10 pm - 10:25 pmSRQ-MDW
4h 15m1 stop
Southwest Logo
7:45 am - 4:35 pmMDW-SRQ
7h 50m2 stops
$322Southwest
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Wed, Oct 15 - Wed, Oct 22
Delta Logo
8:35 am - 2:38 pmSRQ-MDW
7h 03m1 stop
Delta Logo
12:43 pm - 8:43 pmMDW-SRQ
7h 00m1 stop
$325Delta
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Thu, Dec 25 - Tue, Dec 30
Allegiant Air Logo
6:01 am - 11:16 amSRQ-MDW
6h 15m1 stop
Allegiant Air Logo
5:40 pm - 10:33 pmMDW-SRQ
27h 53m2 stops
$326Allegiant Air
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Fri, Oct 17 - Sun, Oct 19
Allegiant Air Logo
6:11 am - 1:21 pmSRQ-MDW
8h 10m1 stop
Allegiant Air Logo
8:33 pm - 9:51 amMDW-SRQ
36h 18m2 stops
$393Allegiant Air
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Fri, Nov 21 - Sun, Nov 23

Delta flights from Sarasota to Chicago Midway Airport

Our best Delta deals on Sarasota to Chicago Midway Airport flight tickets
Delta
Nov 12
SRQ6:00 amSarasota Bradenton Intl
6h 52m
1 stop
MDW11:52 amChicago Midway
Nov 17
MDW7:02 pmChicago Midway
18h 07m
1 stop
SRQ2:09 pmSarasota Bradenton Intl
$311
Find similar
Delta
Dec 25
SRQ8:35 amSarasota Bradenton Intl
7h 03m
1 stop
MDW2:38 pmChicago Midway
Dec 30
MDW12:43 pmChicago Midway
7h 00m
1 stop
SRQ8:43 pmSarasota Bradenton Intl
$325
Find similar
Delta
Nov 14
SRQ5:01 pmSarasota Bradenton Intl
7h 31m
1 stop
MDW11:32 pmChicago Midway
Nov 17
MDW7:02 pmChicago Midway
18h 07m
1 stop
SRQ2:09 pmSarasota Bradenton Intl
$331
Find similar

Southwest flights from Sarasota to Chicago Midway Airport

Our best Southwest deals on Sarasota to Chicago Midway Airport flight tickets
Southwest
Oct 15
SRQ3:55 pmSarasota Bradenton Intl
2h 45m
MDW5:40 pmChicago Midway
Oct 22
MDW5:25 amChicago Midway
5h 20m
1 stop
SRQ11:45 amSarasota Bradenton Intl
$307
Find similar
Southwest
Oct 15
SRQ3:55 pmSarasota Bradenton Intl
2h 45m
MDW5:40 pmChicago Midway
Oct 22
MDW12:35 pmChicago Midway
8h 20m
2 stops
SRQ9:55 pmSarasota Bradenton Intl
$312
Find similar
Southwest
Oct 15
SRQ3:55 pmSarasota Bradenton Intl
2h 45m
MDW5:40 pmChicago Midway
Oct 18
MDW11:45 amChicago Midway
7h 15m
1 stop
SRQ8:00 pmSarasota Bradenton Intl
$315
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 September 18, 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

Wed 10/15

3:55 pm-5:40 pm

Nonstop2h 45m

Chicago Midway

Wed 10/22

5:25 am-11:45 am

1 stop5h 20m

$307

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Wed 11/12

6:00 am-11:52 am

1 stop6h 52m

Chicago Midway

Mon 11/17

7:02 pm-2:09 pm

1 stop18h 07m

$311

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Wed 10/15

3:55 pm-5:40 pm

Nonstop2h 45m

Chicago Midway

Wed 10/22

12:35 pm-9:55 pm

2 stops8h 20m

$312

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Wed 10/15

3:55 pm-5:40 pm

Nonstop2h 45m

Chicago Midway

Sat 10/18

11:45 am-8:00 pm

1 stop7h 15m

$315

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Fri 10/17

3:35 pm-5:20 pm

Nonstop2h 45m

Chicago Midway

Tue 10/21

1:40 pm-5:10 pm

Nonstop2h 30m

$317

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Wed 10/15

3:55 pm-5:40 pm

Nonstop2h 45m

Chicago Midway

Sat 10/18

12:50 pm-9:30 pm

2 stops7h 40m

$320

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Wed 10/15

7:10 pm-10:25 pm

1 stop4h 15m

Chicago Midway

Wed 10/22

7:45 am-4:35 pm

2 stops7h 50m

$322

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Thu 12/25

8:35 am-2:38 pm

1 stop7h 03m

Chicago Midway

Tue 12/30

12:43 pm-8:43 pm

1 stop7h 00m

$325

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Fri 10/17

6:01 am-11:16 am

1 stop6h 15m

Chicago Midway

Sun 10/19

5:40 pm-10:33 pm

2 stops27h 53m

$326

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Fri 11/21

6:11 am-1:21 pm

1 stop8h 10m

Chicago Midway

Sun 11/23

8:33 pm-9:51 am

2 stops36h 18m

$393

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, Tuesday 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 $454.

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 $391 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $703. 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.

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

$168

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 $168. The best round-trip flight deal from Sarasota to Chicago Midway Airport found on momondo in the last 72 hours is $349.
The fastest flight from Sarasota to Chicago Midway Airport takes 2h 40m
Direct flights go from Sarasota to Chicago Midway Airport every day.
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  • 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
4,242 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 5 flights on this route every week with an average price of $387. 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
Lansing
Portage
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.

An easier way to manage your Chicago Midway Airport trip

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