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$66+ Cheap flights from Sarasota (SRQ) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
SRQ — CHI
Jun 26 — Jul 31
Fri 6/26
Fri 7/3
1 adult, Economy
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Find cheap flights from Sarasota to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

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Cheapflights Tip: The best prices from Sarasota Bradenton Intl to Chicago are usually found in August or April, booked 26 days in advance, depart on a Saturday or Thursday and return on a Thursday

Cheap flight deals from Sarasota to Chicago

Cheapest flights from Sarasota to Chicago
Explore the most affordable flight options available from Sarasota to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 27, 2026.

This Southwest deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2211:30 am
SRQ
-
MDW
1 stop6h 10m
Southwest
Mon 8/2412:20 pm
MDW
-
SRQ
Nonstop2h 35m
Southwest
Deal found 5/24$279
This Booking.com deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:45 am
SRQ
-
RFD
Nonstop2h 54m
Allegiant Air
Sat 6/69:07 am
RFD
-
SRQ
Nonstop2h 45m
Allegiant Air
Deal found 5/25$282
This Kiwi.com deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/51:16 pm
SRQ
-
RFD
2 stops19h 33m
Allegiant Air
Wed 7/2911:19 am
RFD
-
SRQ
Nonstop2h 42m
Allegiant Air
Deal found 5/27$287
This Delta deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1712:50 pm
SRQ
-
MDW
1 stop4h 26m
Delta
Tue 6/306:00 am
MDW
-
SRQ
1 stop4h 45m
Delta
Deal found 5/26$288
This Delta deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/206:00 am
SRQ
-
MDW
1 stop6h 51m
Delta
Mon 8/246:05 am
MDW
-
SRQ
1 stop5h 18m
Delta
Deal found 5/24$289
This Delta deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:00 pm
SRQ
-
ORD
1 stop4h 50m
Delta
Mon 8/248:02 am
ORD
-
SRQ
1 stop6h 20m
Delta
Deal found 5/27$289
This Southwest deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/237:25 am
SRQ
-
MDW
1 stop7h 35m
Southwest
Tue 6/307:55 am
MDW
-
SRQ
Nonstop2h 50m
Southwest
Deal found 5/26$292
This Kiwi.com deal was found by Cheapflights users on 5/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/3012:17 pm
SRQ
-
MDW
2 stops33h 14m
Allegiant Air
Thu 8/62:49 pm
MDW
-
SRQ
1 stop25h 06m
Allegiant Air
Deal found 5/27$295
This United Airlines deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/74:30 pm
SRQ
-
ORD
Nonstop3h 16m
United Airlines
Wed 7/1511:10 am
ORD
-
SRQ
Nonstop3h 02m
United Airlines
Deal found 5/24$296
This Delta deal was found by Cheapflights users on 5/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/45:00 pm
SRQ
-
ORD
1 stop8h 02m
Delta
Tue 8/113:31 pm
ORD
-
SRQ
1 stop6h 26m
Delta
Deal found 5/25$298
This Kiwi.com deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/912:55 pm
SRQ
-
RFD
2 stops19h 54m
Allegiant Air
Sat 7/119:05 am
RFD
-
SRQ
Nonstop2h 42m
Allegiant Air
Deal found 5/26$305
This Kiwi.com deal was found by Cheapflights users on 5/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/186:31 am
SRQ
-
RFD
Nonstop2h 44m
Allegiant Air
Sat 7/2512:58 pm
RFD
-
SRQ
2 stops33h 45m
Allegiant Air
Deal found 5/26$306

Find flight deals from Sarasota to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Sarasota (SRQ) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$279
(Southwest)

One-way from

$66
(Kiwi.com)

Popular in

November

Cheapest in

August

Average price

$396

Good round-trip deal

$207 or less

Good one-way deal

$206 or less
Provider with most accurate pricing for Sarasota Bradenton Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Sarasota Bradenton Intl-Chicago (CHI) flights.
Search Deals
From Sarasota Bradenton Intl to Chicago (CHI)
Search Deals
One-way flight from Sarasota Bradenton Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Sarasota Bradenton Intl to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Sarasota Bradenton Intl to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Sarasota to Chicago 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, Cheapflights users made 2,558,603 searches. Data last updated May 27, 2026.
Use the filters below to find and compare flights from Sarasota to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Sat 8/22

11:30 am-4:40 pm

1 stop6h 10m

Chicago Midway

Mon 8/24

12:20 pm-3:55 pm

Nonstop2h 35m

$279

SarasotaChicago

SRQ - RFD

SRQRFD

Sarasota Bradenton Intl

Sat 7/11

6:31 am-8:15 am

Nonstop2h 44m

Chicago Greater Rockford

Sun 7/12

11:27 am-10:53 pm

2 stops34h 26m

$305

SarasotaChicago

SRQ - RFD

SRQRFD

Sarasota Bradenton Intl

Sat 7/18

6:31 am-8:15 am

Nonstop2h 44m

Chicago Greater Rockford

Sat 7/25

12:58 pm-11:43 pm

2 stops33h 45m

$306

SarasotaChicago

SRQ - RFD

SRQRFD

Sarasota Bradenton Intl

Wed 7/8

8:45 am-10:29 am

Nonstop2h 44m

Chicago Greater Rockford

Sun 7/12

11:27 am-10:53 pm

2 stops34h 26m

$316

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Wed 10/21

7:05 am-11:56 am

1 stop5h 51m

Chicago Midway

Sun 10/25

6:00 am-12:34 pm

1 stop5h 34m

$324

SarasotaChicago

SRQ - RFD

SRQRFD

Sarasota Bradenton Intl

Thu 10/15

8:01 am-9:51 am

Nonstop2h 50m

Chicago Greater Rockford

Mon 10/19

6:13 pm-11:09 am

2 stops39h 56m

$325
Quickest round-trip

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Sat 6/27

4:35 pm-6:15 pm

Nonstop2h 40m

Chicago Midway

Wed 7/15

7:55 am-11:45 am

Nonstop2h 50m

$325

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Wed 6/17

6:00 am-10:09 am

1 stop5h 09m

Chicago Midway

Tue 6/30

6:00 am-11:45 am

1 stop4h 45m

$328

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Sat 8/22

4:25 pm-6:36 pm

Nonstop3h 11m

Chicago O'Hare Intl

Mon 8/24

11:10 am-3:10 pm

Nonstop3h 00m

$330

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Tue 9/8

6:00 am-9:50 am

1 stop4h 50m

Chicago Midway

Sun 9/13

5:25 pm-11:59 pm

1 stop5h 34m

$334

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/27

Showing 1-10 of 60 resultsSorted by cheapest first
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Compare providers for flights from Sarasota to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Sarasota to Chicago in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Sarasota-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Sarasota-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Sarasota-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Sarasota-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Sarasota-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Sarasota to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Sarasota with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Sarasota to Chicago

What is the cheapest month to book a flight from Sarasota to Chicago?

Currently, August is the cheapest month in which you can book a flight from Sarasota to Chicago (average of $58). Flying from Sarasota to Chicago in April is currently the most expensive (average of $237). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from SRQ to CHI?

Find hourly flight availability from Sarasota to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 27, 2026.

It’s typically best to fly out from Sarasota to Chicago in the afternoon. Doing so could potentially save you 19% on the flight price compared to flying at noon, which is usually more expensive.

How much does it cost to fly round-trip from Sarasota to Chicago?

How far ahead should I book a flight from Sarasota to Chicago?

The price you pay for your flight from Sarasota to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 81 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest day to fly from Sarasota to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Sarasota to Chicago. Price data was last updated on May 23, 2026.

Travelers seeking maximum savings on their Sarasota to Chicago flight should consider departing on Saturday evenings when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

The best insider tips for Sarasota to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your Sarasota to Chicago trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Brandon Schultz

Brandon Schultz

Expert on SRQ

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated May 27, 2026.
Get a feel of what it's like to fly with Southwest,United Airlines, andAmerican Airlines from Sarasota to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,265 reviews

Comfort

8.0

Food

7.0

Overall

7.9

Boarding

8.1

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,265 reviews
Southwest
7.9
Good
4,265 reviews

Comfort

8.0

Food

7.0

Overall

7.9

Boarding

8.1

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,749 reviews
Southwest
7.9
Good
4,265 reviews

Comfort

8.0

Food

7.0

Overall

7.9

Boarding

8.1

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,640 reviews
Southwest
7.9
Good
4,265 reviews

Comfort

8.0

Food

7.0

Overall

7.9

Boarding

8.1

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Sarasota to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Sarasota to Chicago?

    For a flight from Sarasota to Chicago, you will be flying from Sarasota Bradenton Intl. Sarasota Bradenton Intl (SRQ) is just 4.3 mi from the center of the city. Sarasota Bradenton Intl is the only Sarasota airport and it handles 4 outbound flights to Chicago per day. 5 airlines have flights to Chicago from Sarasota Bradenton Intl on a regular basis.

  • How long is the flight from Sarasota to Chicago?

    Departing from Sarasota to Chicago will take you 2h 44m. There are 1087 mi between Sarasota and Chicago. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from Sarasota to Chicago round-trip?

    According to our current data, Allegiant Air ($120), Delta ($142), and American Airlines ($239) offers the cheapest pricing from Sarasota to Chicago. Allegiant Air is 69% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Sarasota to Chicago one-way?

    The cheapest airlines for a one-way flight from Sarasota to Chicago are Allegiant Air ($59), Delta ($111), and United Airlines ($123).

  • What are the most popular routes from Sarasota to Chicago?

    Most travelers choose Sarasota Bradenton Intl - Chicago O'Hare Intl, Sarasota Bradenton Intl - Chicago Midway or Sarasota Bradenton Intl - Chicago Greater Rockford when deciding on the best route from Sarasota to Chicago.

  • What are the most reliable airlines from Sarasota to Chicago?

    Before booking your flight to Chicago from Sarasota, check out the most reliable airlines to get you to your destination on time: Envoy Air (100%), Air Canada (75%), Emirates( 72%).

  • What are the cheapest flights from Sarasota to Chicago?

    Looking at all options, your cheapest flight can be booked for $146. While the most popular route (Sarasota Bradenton Intl - Chicago O'Hare Intl) can be booked for $237 on average, our data indicates $417 when flying from Sarasota to Chicago.

  • Can I find deals for flights from Sarasota to Chicago that include hotel bookings?

    Yes. In addition to deals on Sarasota to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Sarasota to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Sarasota to Chicago.

  • Can I find deals for business class flights from Sarasota to Chicago?

    Yes. Cheapflights offers flight deals from Sarasota to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Sarasota to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Sarasota to Chicago (average of $58). Flying from Sarasota to Chicago in April is currently the most expensive (average of $237). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Alternative routes for Sarasota to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Sarasota to Chicago

Discover the top 5 airlines that operate flights from Sarasota to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$120Average$202FlexibilityNo cancel feeOn-time88%
DeltaCheapest$142Average$350FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$239Average$392FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$277Average$421FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$282Average$433FlexibilityNo cancel feeOn-time63%

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