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Cheap flights from Chicago to Sarasota from $83

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Sarasota departing on 10/16. 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

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Find the cheapest flights from Chicago to Sarasota

Cheap round-trip flights

Frontier Logo
8:26 am - 7:43 pmORD-SRQ
10h 17m1 stop
Frontier Logo
8:30 pm - 7:26 amSRQ-ORD
11h 56m1 stop
$209Frontier
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Thu, Oct 30 - Sun, Nov 2
JetBlue Logo
9:00 am - 6:38 pmORD-SRQ
8h 38m1 stop
JetBlue Logo
12:45 pm - 8:59 pmSRQ-ORD
9h 14m1 stop
$211JetBlue
Find Deal
Thu, Jan 22 - Sun, Jan 25
Southwest Logo
6:25 am - 2:45 pmMDW-SRQ
7h 20m1 stop
Southwest Logo
7:10 pm - 10:25 pmSRQ-MDW
4h 15m1 stop
$264Southwest
Find Deal
Wed, Oct 1 - Tue, Oct 7
Southwest Logo
6:25 am - 2:45 pmMDW-SRQ
7h 20m1 stop
Southwest Logo
7:10 am - 2:25 pmSRQ-MDW
8h 15m2 stops
$269Southwest
Find Deal
Wed, Oct 1 - Tue, Oct 7
American Airlines Logo
8:03 am - 12:20 pmORD-SRQ
3h 17mnonstop
American Airlines Logo
5:34 pm - 7:45 pmSRQ-ORD
3h 11mnonstop
$288American Airlines
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Wed, Jan 14 - Wed, Feb 18
American Airlines Logo
2:50 pm - 11:22 pmORD-SRQ
7h 32m1 stop
American Airlines Logo
11:40 am - 1:46 pmSRQ-ORD
3h 06mnonstop
$289American Airlines
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Thu, Nov 6 - Fri, Nov 14
United Airlines Logo
7:25 am - 11:35 pmORD-SRQ
15h 10m2 stops
United Airlines Logo
4:22 pm - 6:25 pmSRQ-ORD
3h 03mnonstop
$290United Airlines
Find Deal
Sat, Oct 11 - Sat, Oct 18
Delta Logo
6:00 am - 7:18 pmORD-SRQ
12h 18m2 stops
Delta Logo
5:15 pm - 11:58 pmSRQ-ORD
7h 43m1 stop
$295Delta
Find Deal
Tue, Oct 7 - Tue, Oct 14
United Airlines Logo
7:20 am - 11:09 amORD-SRQ
2h 49mnonstop
United Airlines Logo
4:15 pm - 6:28 pmSRQ-ORD
3h 13mnonstop
$297United Airlines
Find Deal
Tue, Nov 11 - Wed, Nov 19
Delta Logo
11:00 am - 4:00 pmMDW-SRQ
4h 00m1 stop
Delta Logo
5:15 pm - 10:14 pmSRQ-MDW
5h 59m1 stop
$298Delta
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Sat, Oct 4 - Wed, Oct 15

Southwest flights from Chicago to Sarasota

Our best Southwest deals on Chicago to Sarasota flight tickets
Southwest
Oct 1
MDW6:25 amChicago Midway
7h 20m
1 stop
SRQ2:45 pmSarasota Bradenton Intl
Oct 7
SRQ7:10 pmSarasota Bradenton Intl
4h 15m
1 stop
MDW10:25 pmChicago Midway
$264
Find similar
Southwest
Oct 1
MDW6:25 amChicago Midway
7h 20m
1 stop
SRQ2:45 pmSarasota Bradenton Intl
Oct 7
SRQ7:10 amSarasota Bradenton Intl
8h 15m
2 stops
MDW2:25 pmChicago Midway
$269
Find similar
Southwest
Oct 23
MDW1:30 pmChicago Midway
2h 35m
SRQ5:05 pmSarasota Bradenton Intl
Oct 29
SRQ3:55 pmSarasota Bradenton Intl
2h 45m
MDW5:40 pmChicago Midway
$305
Find similar

American Airlines flights from Chicago to Sarasota

Our best American Airlines deals on Chicago to Sarasota flight tickets
American Airlines
Jan 14
ORD8:03 amChicago O'Hare Intl
3h 17m
SRQ12:20 pmSarasota Bradenton Intl
Feb 18
SRQ5:34 pmSarasota Bradenton Intl
3h 11m
ORD7:45 pmChicago O'Hare Intl
$288
Find similar
American Airlines
Nov 6
ORD2:50 pmChicago O'Hare Intl
7h 32m
1 stop
SRQ11:22 pmSarasota Bradenton Intl
Nov 14
SRQ11:40 amSarasota Bradenton Intl
3h 06m
ORD1:46 pmChicago O'Hare Intl
$289
Find similar
American Airlines
Jan 15
ORD8:03 amChicago O'Hare Intl
3h 17m
SRQ12:20 pmSarasota Bradenton Intl
Jan 20
SRQ12:50 pmSarasota Bradenton Intl
3h 24m
ORD3:14 pmChicago O'Hare Intl
$296
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Sarasota 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 15, 2025.
Use the filters below to find and compare flights from Chicago to Sarasota that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Thu 10/30

8:26 am-7:43 pm

1 stop10h 17m

Sarasota Bradenton Intl

Sun 11/2

8:30 pm-7:26 am

1 stop11h 56m

$209

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Thu 1/22

9:00 am-6:38 pm

1 stop8h 38m

Sarasota Bradenton Intl

Sun 1/25

12:45 pm-8:59 pm

1 stop9h 14m

$211

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Wed 10/1

6:25 am-2:45 pm

1 stop7h 20m

Sarasota Bradenton Intl

Tue 10/7

7:10 pm-10:25 pm

1 stop4h 15m

$264

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Wed 10/1

6:25 am-2:45 pm

1 stop7h 20m

Sarasota Bradenton Intl

Tue 10/7

7:10 am-2:25 pm

2 stops8h 15m

$269

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Wed 1/14

8:03 am-12:20 pm

Nonstop3h 17m

Sarasota Bradenton Intl

Wed 2/18

5:34 pm-7:45 pm

Nonstop3h 11m

$288

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Thu 11/6

2:50 pm-11:22 pm

1 stop7h 32m

Sarasota Bradenton Intl

Fri 11/14

11:40 am-1:46 pm

Nonstop3h 06m

$289

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Sat 10/11

7:25 am-11:35 pm

2 stops15h 10m

Sarasota Bradenton Intl

Sat 10/18

4:22 pm-6:25 pm

Nonstop3h 03m

$290

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Tue 10/7

6:00 am-7:18 pm

2 stops12h 18m

Sarasota Bradenton Intl

Tue 10/14

5:15 pm-11:58 pm

1 stop7h 43m

$295

ChicagoSarasota

ORD - SRQ

ORDSRQ

Chicago O'Hare Intl

Tue 11/11

7:20 am-11:09 am

Nonstop2h 49m

Sarasota Bradenton Intl

Wed 11/19

4:15 pm-6:28 pm

Nonstop3h 13m

$297

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Sat 10/4

11:00 am-4:00 pm

1 stop4h 00m

Sarasota Bradenton Intl

Wed 10/15

5:15 pm-10:14 pm

1 stop5h 59m

$298

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 Sarasota from

How to get the cheapest flight ticket from Chicago to Sarasota

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 Chicago and Sarasota?

What is the cheapest month to fly to Sarasota?

The cheapest month to fly to Sarasota from Chicago is in January. Flight prices, which tend to average around $266, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of January, then book flights to Sarasota from Chicago during February instead. Flights to Sarasota in February, while not as cheap as those in January, still average around $304.

What is the cheapest day to depart on your flight to Sarasota?

The cheapest day to depart from Chicago to Sarasota is on a Wednesday when prices can be found for as low as $297. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Chicago to Sarasota for around $444.

What is the cheapest time of day to depart on your flight to Sarasota?

The cheapest time of day to fly to Sarasota is in the afternoon when flights can be purchased for as low as $172. In the evening is when there is more demand to fly to Sarasota, so prices are often more expensive at around $423 per ticket.

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

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

How far in advance should I book a flight to Sarasota?

You are more likely to see cheaper flights to Sarasota from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Sarasota for around $372 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Sarasota from Chicago for as low as $290 on momondo.

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

There are 4 cabin classes available to choose from on Chicago to Sarasota Bradenton Intl 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 Chicago to Sarasota flights?

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

How have Chicago to Sarasota flight prices changed over time?

As of September 2025, prices for Chicago to Sarasota flights are approximately 45% cheaper when compared to flights at the same time last year.

When to book flights from Chicago to Sarasota

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

Cheap Chicago to Sarasota (CHI to SRQ) flight deals and tips

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

Best Price Found

$138

Fastest flight time

2h 30m

Direct flights

Every day

Airports in Sarasota

1 airport
The best one-way flight to Sarasota from Chicago in the past 72 hours is $138. The best round-trip flight deal from Chicago to Sarasota found on momondo in the last 72 hours is $323.
The fastest flight from Chicago to Sarasota takes 2h 30m
Direct flights go from Chicago to Sarasota every day.
There is 1 airport near Sarasota: Sarasota Bradenton Intl (SRQ)
Search flight deals

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

    The straight-line distance from Chicago to Sarasota Bradenton Intl is 1044.3 mi. A reasonable flight in good conditions will take 2h 35m.

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

    Prices for flights from Chicago to Sarasota Bradenton Intl Airport were last updated today.

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

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to Sarasota Bradenton Intl Airport.

  • What documentation or ID do you need to fly to Sarasota Bradenton Intl Airport?

    The travel and health documents required for your trip to Sarasota Bradenton Intl Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Sarasota Bradenton Intl Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

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

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

Best airlines flying from Chicago to Sarasota

Compare and see reviews for airlines that fly from Chicago to Sarasota with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $37Free CancellationRating
5.8
3,172 reviews
Search Frontier flights
Allegiant AirPriceFrom $89Free CancellationRating
7.2
699 reviews
Search Allegiant Air flights
DeltaPriceFrom $196Free CancellationRating
7.9
7,954 reviews
Search Delta flights
American AirlinesPriceFrom $199Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $232Free CancellationRating
7.4
8,929 reviews
Search United Airlines flights
SouthwestPriceFrom $287Free CancellationRating
8.0
4,242 reviews
Search Southwest flights

  • Southwest Flights From Chicago to Sarasota

    Southwest flies from Chicago to Sarasota around 5 times per week, with 4,242 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Chicago to Sarasota in the last 72 hours was $287 (round-trip), much lower than the average airfare cost of $412 for Southwest flights on this route.

  • United Airlines Flights From Chicago to Sarasota

    Another popular option for Chicago to Sarasota flights is United Airlines (7.4/10, 8,929 ratings). United Airlines flies from Chicago to Sarasota around 7 times per week, with deals starting from $232 round-trip and rising to an average price of around $426.

Traveling to a place near Sarasota?

Book flights to Sarasota if you plan to visit one of these locations
Siesta Key
Venice
Nokomis

Why use momondo?

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

Finding the right flight to Sarasota from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Sarasota quick and easy, saving you time and money.

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

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

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

momondo helps you find the best flight between Chicago and Sarasota by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

If you are simply researching potential flights to Sarasota, momondo offers a useful price alert feature which will track prices for flights to Sarasota from Chicago and alert you when they change.

An easier way to manage your Sarasota trip

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