What airlines fly to Chicago?

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to Chicago from Sarasota according to our data. American Airlines is the first choice among our users, with 31% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Sarasota Bradenton Intl to Chicago?

Allegiant Air, Southwest, and American Airlines are the most popular carriers operating from Sarasota Bradenton Intl to Chicago

How many flights depart from Sarasota to Chicago on average per day?

The number of flights available between Sarasota and Chicago is 10 per day as of January 2026. The most frequent departure time is 4:00PM, with 67% of daily flights leaving in the afternoon.

How many flights depart from Sarasota to Chicago on average per week?

As of January 2026, there are 72 flights per week flying from Sarasota to Chicago. The most common day of the week flights depart is Mon, with 17% of flights taking off on this day.

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

Prices for flights from Sarasota Bradenton Intl Airport to Chicago refresh daily.

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

As of January 2026, there are 6 operators available to choose from for flights from Sarasota Bradenton Intl Airport to Chicago.

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

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Sarasota Bradenton Intl Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The required travel and health documents for your Chicago 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. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$86 Cheap Flights from Sarasota to Chicago in 2026

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Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

9:00 am - 11:00 am

SRQ

RFD

3h 00mnonstop

11:50 am - 3:30 pm

RFD

SRQ

2h 40mnonstop

$182Allegiant Air

Thu, Apr 16 - Sun, Apr 19

7:59 pm - 10:46 pm

SRQ

ORD

27h 47m

2 stops

5:25 am - 9:22 pm

ORD

SRQ

14h 57m

1 stop

$285Multiple Airlines

Sat, Jan 31 - Sun, Feb 8

9:20 am - 11:33 am

SRQ

ORD

3h 13mnonstop

4:20 pm - 8:25 pm

ORD

SRQ

3h 05mnonstop

$319United Airlines

Wed, Apr 15 - Tue, Apr 21

9:20 am - 11:33 am

SRQ

ORD

3h 13mnonstop

5:49 am - 3:47 pm

ORD

SRQ

8h 58m

1 stop

$329United Airlines

Wed, Apr 15 - Tue, Apr 21

12:35 pm - 2:30 pm

SRQ

MDW

2h 55mnonstop

2:00 pm - 5:40 pm

MDW

SRQ

2h 40mnonstop

$331Southwest

Wed, Feb 25 - Sat, Feb 28

5:45 pm - 8:00 pm

SRQ

ORD

3h 15mnonstop

1:15 pm - 4:59 pm

ORD

SRQ

2h 44mnonstop

$331American Airlines

Wed, Feb 18 - Mon, Feb 23

5:04 pm - 12:45 am

SRQ

ORD

8h 41m

1 stop

3:35 pm - 11:59 pm

ORD

SRQ

7h 24m

1 stop

$339United Airlines

Wed, Apr 15 - Tue, Apr 21

10:00 am - 4:45 pm

SRQ

MDW

7h 45m

1 stop

6:55 pm - 10:35 pm

MDW

SRQ

2h 40mnonstop

$341Southwest

Wed, Feb 25 - Sat, Feb 28

12:52 pm - 3:04 pm

SRQ

ORD

3h 12mnonstop

6:40 am - 1:43 pm

ORD

SRQ

6h 03m

1 stop

$341American Airlines

Wed, Feb 18 - Mon, Feb 23

12:01 pm - 6:21 pm

SRQ

ORD

7h 20m

1 stop

7:00 pm - 10:51 am

ORD

SRQ

14h 51m

1 stop

$345Sun Country Air

Thu, Apr 16 - Sun, Apr 19

Delta flights from Sarasota to Chicago

Our best Delta deals on Sarasota to Chicago flight tickets

Delta

Feb 3

SRQ11:28 amSarasota Bradenton Intl

12h 06m

1 stop

ORD10:34 pmChicago O'Hare Intl

Feb 4

ORD7:10 amChicago O'Hare Intl

10h 07m

1 stop

SRQ6:17 pmSarasota Bradenton Intl

$323

Delta

Feb 18

SRQ6:00 amSarasota Bradenton Intl

4h 54m

1 stop

MDW9:54 amChicago Midway

Feb 23

MDW12:45 pmChicago Midway

4h 25m

1 stop

SRQ6:10 pmSarasota Bradenton Intl

$351

Delta

Apr 28

SRQ12:40 pmSarasota Bradenton Intl

5h 01m

1 stop

ORD4:41 pmChicago O'Hare Intl

May 6

ORD8:15 amChicago O'Hare Intl

5h 00m

1 stop

SRQ2:15 pmSarasota Bradenton Intl

$363

JetBlue flights from Sarasota to Chicago

Our best JetBlue deals on Sarasota to Chicago flight tickets

JetBlue

Feb 5

SRQ5:38 pmSarasota Bradenton Intl

26h 53m

1 stop

ORD7:31 pmChicago O'Hare Intl

Feb 9

ORD9:40 amChicago O'Hare Intl

29h 02m

1 stop

SRQ3:42 pmSarasota Bradenton Intl

$329

JetBlue

Feb 6

SRQ5:38 pmSarasota Bradenton Intl

26h 53m

1 stop

ORD7:31 pmChicago O'Hare Intl

Feb 9

ORD9:40 amChicago O'Hare Intl

29h 02m

1 stop

SRQ3:42 pmSarasota Bradenton Intl

$335

JetBlue

Mar 7

SRQ12:40 pmSarasota Bradenton Intl

11h 20m

1 stop

ORD11:00 pmChicago O'Hare Intl

Mar 10

ORD6:04 amChicago O'Hare Intl

8h 40m

1 stop

SRQ3:44 pmSarasota Bradenton Intl

$348

Fly from

Fly to

Route

Depart

Return

Price

SarasotaChicago

SRQ - RFD

SRQRFD

Sarasota Bradenton Intl

Thu 4/16

9:00 am-11:00 am

Nonstop3h 00m

Chicago Greater Rockford

Sun 4/19

11:50 am-3:30 pm

Nonstop2h 40m

$182

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Sat 1/31

7:59 pm-10:46 pm

2 stops27h 47m

Chicago O'Hare Intl

Sun 2/8

5:25 am-9:22 pm

1 stop14h 57m

$285

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Wed 4/15

9:20 am-11:33 am

Nonstop3h 13m

Chicago O'Hare Intl

Tue 4/21

4:20 pm-8:25 pm

Nonstop3h 05m

$319

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Wed 4/15

9:20 am-11:33 am

Nonstop3h 13m

Chicago O'Hare Intl

Tue 4/21

5:49 am-3:47 pm

1 stop8h 58m

$329

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Wed 2/25

12:35 pm-2:30 pm

Nonstop2h 55m

Chicago Midway

Sat 2/28

2:00 pm-5:40 pm

Nonstop2h 40m

$331

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Wed 2/18

5:45 pm-8:00 pm

Nonstop3h 15m

Chicago O'Hare Intl

Mon 2/23

1:15 pm-4:59 pm

Nonstop2h 44m

$331

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Wed 4/15

5:04 pm-12:45 am

1 stop8h 41m

Chicago O'Hare Intl

Tue 4/21

3:35 pm-11:59 pm

1 stop7h 24m

$339

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Wed 2/25

10:00 am-4:45 pm

1 stop7h 45m

Chicago Midway

Sat 2/28

6:55 pm-10:35 pm

Nonstop2h 40m

$341

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Wed 2/18

12:52 pm-3:04 pm

Nonstop3h 12m

Chicago O'Hare Intl

Mon 2/23

6:40 am-1:43 pm

1 stop6h 03m

$341

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Thu 4/16

12:01 pm-6:21 pm

1 stop7h 20m

Chicago O'Hare Intl

Sun 4/19

7:00 pm-10:51 am

1 stop14h 51m

$345

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Sarasota to Chicago

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

Prices

Airlines

Other information

What is the typical price of a round-trip flight between Sarasota and Chicago?

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Sarasota, with most prices found around $129. If you’re not able to fly to Chicago in February, then March is your next best option. Flight prices from Sarasota to Chicago during March average around $265.

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

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $382. This is often the case because there is less demand to fly during this day of the week. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from Sarasota to Chicago for around $552.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Sarasota to Chicago during this time can be as low as $314. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $425.

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

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

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

You are more likely to see cheaper flights to Chicago from Sarasota when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $372 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Sarasota for as low as $252 on momondo.

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

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

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

How have Sarasota to Chicago flight prices changed over time?

As of January 2026, prices for Sarasota to Chicago flights are approximately 81% more expensive when compared to flights at the same time last year.

When to book flights from Sarasota to Chicago

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

Estimated round-trip price

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

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

Best Price Found	$196
Fastest flight time	2h 40m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Sarasota in the past 72 hours is $196. The best round-trip flight deal from Sarasota to Chicago found on momondo in the last 72 hours is $139.

The fastest flight from Sarasota to Chicago takes 2h 40m

Direct flights go from Sarasota to Chicago every day.

There are 3 airports in Chicago. From Sarasota there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD).

Search flight deals

How far is Sarasota Bradenton Intl to Chicago by plane?
A flight from Sarasota Bradenton Intl to Chicago will travel around 1044.3 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?
Prices for flights from Sarasota Bradenton Intl Airport to Chicago refresh daily.
How many operators does momondo search for flights from Sarasota Bradenton Intl Airport to Chicago?
As of January 2026, there are 6 operators available to choose from for flights from Sarasota Bradenton Intl Airport to Chicago.
How old do you have to be to fly from Sarasota Bradenton Intl Airport to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Sarasota Bradenton Intl Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago 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. 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?
Based on momondo bookings for flights between Sarasota and Chicago, the leading plane model is Airbus A320-100/200, making up 15.06% of the total bookings. Other popular models include Boeing 737 MAX 8 with 13.51%, Boeing 737-800 with 13.51%, and Airbus A319 with 11.97%.
What is the most popular airline from Sarasota to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Sarasota to Chicago is Southwest (43% of total bookings). The next most popular airlines are United Airlines (38%), American Airlines (10%), and Frontier (9%).

Best airlines flying from Sarasota to Chicago

Compare and see reviews for airlines that fly from Sarasota to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $50	Free Cancellation	Rating 5.7 3,055 reviews	Search Frontier flights
Allegiant Air	PriceFrom $115	Free Cancellation	Rating 7.2 705 reviews	Search Allegiant Air flights
Delta	PriceFrom $138	Free Cancellation	Rating 7.9 8,087 reviews	Search Delta flights
United Airlines	PriceFrom $180	Free Cancellation	Rating 7.4 9,188 reviews	Search United Airlines flights
American Airlines	PriceFrom $217	Free Cancellation	Rating 7.2 11,169 reviews	Search American Airlines flights
Southwest	PriceFrom $267	Free Cancellation	Rating 8.0 4,266 reviews	Search Southwest flights

Southwest Flights From Sarasota to Chicago
Across 9 Southwest flights from Sarasota to Chicago this week, the average price was $375, with the best Southwest deals starting from $267 round-trip. 4,266 users have rated Southwest on momondo, with an average score of 8.0/10.
United Airlines Flights From Sarasota to Chicago
Across 9,191 United Airlines reviews on momondo, the average score is 7.4/10. United Airlines flies from Sarasota to Chicago about 14 times each week, with ticket deals ranging from $180 to $411. Price data is based on momondo searches in the last 72 hours.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Sarasota.

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 you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Sarasota.

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 trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Cheap flights from Sarasota to Chicago from $125

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 1/29. 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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Delta flights from Sarasota to Chicago

Our best Delta deals on Sarasota to Chicago flight tickets

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Our best JetBlue deals on Sarasota to Chicago flight tickets

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Use the filters below to find and compare flights from Sarasota to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Sarasota to Chicago

What is the typical price of a round-trip flight between Sarasota and Chicago?

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Sarasota, with most prices found around $129. If you’re not able to fly to Chicago in February, then March is your next best option. Flight prices from Sarasota to Chicago during March average around $265.

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

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Sarasota to Chicago during this time can be as low as $314. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $425.

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

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

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

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

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

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

How have Sarasota to Chicago flight prices changed over time?

As of January 2026, prices for Sarasota to Chicago flights are approximately 81% more expensive when compared to flights at the same time last year.

What is the cheapest airline that flies from Sarasota Bradenton Intl to Chicago?

Allegiant Air, Southwest, and American Airlines are the most popular carriers operating from Sarasota Bradenton Intl to Chicago

What airlines fly to Chicago?

How many flights depart from Sarasota to Chicago on average per day?

The number of flights available between Sarasota and Chicago is 10 per day as of January 2026. The most frequent departure time is 4:00PM, with 67% of daily flights leaving in the afternoon.

How many flights depart from Sarasota to Chicago on average per week?

As of January 2026, there are 72 flights per week flying from Sarasota to Chicago. The most common day of the week flights depart is Mon, with 17% of flights taking off on this day.

When to book flights from Sarasota to Chicago

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

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

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

How far is Sarasota Bradenton Intl to Chicago by plane?

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

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

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

What documentation or ID do you need to fly to Chicago?

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

What is the most popular airline from Sarasota to Chicago?

Best airlines flying from Sarasota to Chicago

Compare and see reviews for airlines that fly from Sarasota to Chicago with momondo

Southwest Flights From Sarasota to Chicago

United Airlines Flights From Sarasota to Chicago

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago