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.

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

The number of flights available between Sarasota and Chicago is 5 per day as of August 2025. The most frequent departure time is 4:00PM, with 52% of daily flights leaving in the afternoon.

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

Allegiant Air, Frontier, and Sun Country Air are the most popular carriers operating from Sarasota Bradenton Intl to Chicago

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

As of August 2025, there are 39 flights per week flying from Sarasota to Chicago. The most common day of the week flights depart is Sat, with 23% 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 August 2025, 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.

$57 Cheap Flights from Sarasota to Chicago in 2025

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Find the cheapest flights from Sarasota to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

8:30 pm - 7:20 amSRQ-MDW

11h 50m1 stop

8:15 am - 7:31 pmMDW-SRQ

10h 16m1 stop

$218Frontier

Find Deal

Thu, Oct 23 - Sun, Oct 26

7:01 am - 8:54 amSRQ-RFD

2h 53mnonstop

7:03 pm - 10:39 pmRFD-SRQ

2h 36mnonstop

$252Allegiant Air

Find Deal

Sun, Nov 23 - Sat, Nov 29

4:00 pm - 5:45 pmSRQ-MDW

2h 45mnonstop

1:45 pm - 5:20 pmMDW-SRQ

2h 35mnonstop

$277Southwest

Find Deal

Sat, Aug 23 - Mon, Aug 25

4:37 pm - 6:41 pmSRQ-ORD

3h 04mnonstop

11:22 am - 3:15 pmORD-SRQ

2h 53mnonstop

$277United Airlines

Find Deal

Wed, Sep 3 - Wed, Sep 10

11:40 am - 1:25 pmSRQ-MDW

2h 45mnonstop

1:55 pm - 5:30 pmMDW-SRQ

2h 35mnonstop

$286Southwest

Find Deal

Mon, Aug 25 - Sun, Aug 31

4:37 pm - 6:41 pmSRQ-ORD

3h 04mnonstop

11:22 am - 3:15 pmORD-SRQ

2h 53mnonstop

$286United Airlines

Find Deal

Thu, Sep 4 - Sun, Sep 7

8:37 am - 3:39 pmSRQ-ORD

8h 02m1 stop

1:31 pm - 5:17 pmORD-SRQ

2h 46mnonstop

$296American Airlines

Find Deal

Wed, Dec 17 - Wed, Dec 31

5:03 pm - 9:44 pmSRQ-MDW

5h 41m1 stop

4:25 pm - 11:09 pmMDW-SRQ

5h 44m1 stop

$297Delta

Find Deal

Tue, Aug 26 - Sat, Aug 30

6:00 am - 10:04 amSRQ-ORD

5h 04m1 stop

9:47 am - 3:58 pmORD-SRQ

5h 11m1 stop

$297Delta

Find Deal

Tue, Aug 26 - Wed, Sep 3

5:18 pm - 11:52 pmSRQ-ORD

7h 34m1 stop

5:00 am - 11:32 amORD-SRQ

5h 32m1 stop

$314American Airlines

Find Deal

Sun, Sep 14 - Sun, Sep 21

Sun Country Air flights from Sarasota to Chicago

Our best Sun Country Air deals on Sarasota to Chicago flight tickets

Sun Country Air

Dec 20

SRQ10:43 amSarasota Bradenton Intl

7h 07m

1 stop

ORD4:50 pmChicago O'Hare Intl

Dec 31

ORD11:45 amChicago O'Hare Intl

22h 05m

1 stop

SRQ10:50 amSarasota Bradenton Intl

$259

Find similar

Sun Country Air

Nov 26

SRQ5:04 pmSarasota Bradenton Intl

16h 16m

1 stop

ORD8:20 amChicago O'Hare Intl

Nov 29

ORD8:22 pmChicago O'Hare Intl

12h 33m

1 stop

SRQ9:55 amSarasota Bradenton Intl

$262

Find similar

Sun Country Air

Dec 20

SRQ10:43 amSarasota Bradenton Intl

7h 07m

1 stop

ORD4:50 pmChicago O'Hare Intl

Dec 31

ORD11:45 amChicago O'Hare Intl

22h 05m

1 stop

SRQ10:50 amSarasota Bradenton Intl

$282

Find similar

United Airlines flights from Sarasota to Chicago

Our best United Airlines deals on Sarasota to Chicago flight tickets

United Airlines

Sep 3

SRQ4:37 pmSarasota Bradenton Intl

3h 04m

ORD6:41 pmChicago O'Hare Intl

Sep 10

ORD11:22 amChicago O'Hare Intl

2h 53m

SRQ3:15 pmSarasota Bradenton Intl

$277

Find similar

United Airlines

Sep 4

SRQ4:37 pmSarasota Bradenton Intl

3h 04m

ORD6:41 pmChicago O'Hare Intl

Sep 7

ORD11:22 amChicago O'Hare Intl

2h 53m

SRQ3:15 pmSarasota Bradenton Intl

$286

Find similar

United Airlines

Sep 3

SRQ6:00 amSarasota Bradenton Intl

6h 39m

1 stop

ORD11:39 amChicago O'Hare Intl

Sep 10

ORD11:22 amChicago O'Hare Intl

2h 53m

SRQ3:15 pmSarasota Bradenton Intl

$287

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Fly from

Fly to

Route

Depart

Return

Price

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Thu 10/23

8:30 pm-7:20 am

1 stop11h 50m

Chicago Midway

Sun 10/26

8:15 am-7:31 pm

1 stop10h 16m

$218

SarasotaChicago

SRQ - RFD

SRQRFD

Sarasota Bradenton Intl

Sun 11/23

7:01 am-8:54 am

Nonstop2h 53m

Chicago Greater Rockford

Sat 11/29

7:03 pm-10:39 pm

Nonstop2h 36m

$252

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Sat 8/23

4:00 pm-5:45 pm

Nonstop2h 45m

Chicago Midway

Mon 8/25

1:45 pm-5:20 pm

Nonstop2h 35m

$277

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Wed 9/3

4:37 pm-6:41 pm

Nonstop3h 04m

Chicago O'Hare Intl

Wed 9/10

11:22 am-3:15 pm

Nonstop2h 53m

$277

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Mon 8/25

11:40 am-1:25 pm

Nonstop2h 45m

Chicago Midway

Sun 8/31

1:55 pm-5:30 pm

Nonstop2h 35m

$286

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Thu 9/4

4:37 pm-6:41 pm

Nonstop3h 04m

Chicago O'Hare Intl

Sun 9/7

11:22 am-3:15 pm

Nonstop2h 53m

$286

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Wed 12/17

8:37 am-3:39 pm

1 stop8h 02m

Chicago O'Hare Intl

Wed 12/31

1:31 pm-5:17 pm

Nonstop2h 46m

$296

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Tue 8/26

5:03 pm-9:44 pm

1 stop5h 41m

Chicago Midway

Sat 8/30

4:25 pm-11:09 pm

1 stop5h 44m

$297

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Tue 8/26

6:00 am-10:04 am

1 stop5h 04m

Chicago O'Hare Intl

Wed 9/3

9:47 am-3:58 pm

1 stop5h 11m

$297

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Sun 9/14

5:18 pm-11:52 pm

1 stop7h 34m

Chicago O'Hare Intl

Sun 9/21

5:00 am-11:32 am

1 stop5h 32m

$314

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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 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 $115. If you’re not able to fly to Chicago in February, then January is your next best option. Flight prices from Sarasota to Chicago during January average around $226.

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 $363. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Sarasota to Chicago for around $502.

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 $171. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $440.

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 $387 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 $255 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.

How have Sarasota to Chicago flight prices changed over time?

As of August 2025, prices for Sarasota to Chicago flights are approximately 50% cheaper 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	$88
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 $88. The best round-trip flight deal from Sarasota to Chicago found on momondo in the last 72 hours is $218.

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

Direct flights go from Sarasota to Chicago every day.

There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

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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 August 2025, 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 Boeing 737-700, making up 13.60% of the total bookings. Other popular models include Boeing 737-800 Passenger/BBJ2 (winglets) with 13.10%, Boeing 737-800 with 9.95%, and Airbus A320-100/200 with 8.96%.
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 (36% of total bookings). The next most popular airlines are United Airlines (35%), Frontier (16%), and American Airlines (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 $48	Free Cancellation	Rating 5.8 3,241 reviews	Search Frontier flights
Allegiant Air	PriceFrom $97	Free Cancellation	Rating 7.2 702 reviews	Search Allegiant Air flights
American Airlines	PriceFrom $217	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $222	Free Cancellation	Rating 7.4 8,904 reviews	Search United Airlines flights
Southwest	PriceFrom $267	Free Cancellation	Rating 8.0 4,246 reviews	Search Southwest flights
Delta	PriceFrom $276	Free Cancellation	Rating 8.0 7,983 reviews	Search Delta flights

Southwest Flights From Sarasota to Chicago
Across 8 Southwest flights from Sarasota to Chicago this week, the average price was $386, with the best Southwest deals starting from $267 round-trip. 4,246 users have rated Southwest on momondo, with an average score of 8.0/10.
United Airlines Flights From Sarasota to Chicago
Across 8,904 United Airlines reviews on momondo, the average score is 7.4/10. United Airlines flies from Sarasota to Chicago about 7 times each week, with ticket deals ranging from $222 to $440. Price data is based on momondo searches in the last 72 hours.

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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?

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.

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Cheap flights from Sarasota to Chicago from $88

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 9/15. 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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Big names and deals

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Cheap last minute flights

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Sun Country Air flights from Sarasota to Chicago

Our best Sun Country Air deals on Sarasota to Chicago flight tickets

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Our best United Airlines deals on Sarasota to Chicago flight tickets

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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

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 $115. If you’re not able to fly to Chicago in February, then January is your next best option. Flight prices from Sarasota to Chicago during January average around $226.

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 $171. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $440.

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.

How have Sarasota to Chicago flight prices changed over time?

As of August 2025, prices for Sarasota to Chicago flights are approximately 50% cheaper 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, Frontier, and Sun Country Air 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 5 per day as of August 2025. The most frequent departure time is 4:00PM, with 52% of daily flights leaving in the afternoon.

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

As of August 2025, there are 39 flights per week flying from Sarasota to Chicago. The most common day of the week flights depart is Sat, with 23% 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