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$60+ 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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
SRQ — CHI
Aug 17 — Aug 241
Mon 8/17
Mon 8/24
1 adult, Economy
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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 July 18, 2026.

This Mytrip deal was found by Cheapflights users on 7/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:31 am
SRQ
-
RFD
Nonstop2h 54m
Allegiant Air
Thu 8/2711:54 am
RFD
-
SRQ
Nonstop2h 40m
Allegiant Air
Deal found 7/15$98
This CheapOair deal was found by Cheapflights users on 7/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/179:15 am
SRQ
-
RFD
Nonstop2h 50m
Allegiant Air
Thu 9/2411:55 am
RFD
-
SRQ
Nonstop2h 40m
Allegiant Air
Deal found 7/16$121
This CheapOair deal was found by Cheapflights users on 7/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/179:15 am
SRQ
-
RFD
Nonstop2h 50m
Allegiant Air
Sun 9/2011:55 am
RFD
-
SRQ
Nonstop2h 40m
Allegiant Air
Deal found 7/15$137
This Kiwi.com deal was found by Cheapflights users on 7/16. 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 9/109:15 am
SRQ
-
RFD
Nonstop2h 50m
Allegiant Air
Thu 9/1711:55 am
RFD
-
SRQ
Nonstop2h 40m
Allegiant Air
Deal found 7/16$141
This Mytrip deal was found by Cheapflights users on 7/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/18:30 am
SRQ
-
RFD
Nonstop2h 50m
Allegiant Air
Sun 10/411:12 am
RFD
-
SRQ
Nonstop2h 37m
Allegiant Air
Deal found 7/14$153
This Booking.com deal was found by Cheapflights users on 7/14. 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.
Thu 8/209:15 am
SRQ
-
RFD
Nonstop2h 49m
Allegiant Air
Sun 8/2311:54 am
RFD
-
SRQ
Nonstop2h 40m
Allegiant Air
Deal found 7/14$162
This Southwest deal was found by Cheapflights users on 7/14. 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 8/223:20 pm
SRQ
-
MDW
Nonstop2h 40m
Southwest
Mon 8/2412:20 pm
MDW
-
SRQ
Nonstop2h 35m
Southwest
Deal found 7/14$217
This United Airlines deal was found by Cheapflights users on 7/13. 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 8/44:30 pm
SRQ
-
ORD
Nonstop3h 16m
United Airlines
Tue 8/1111:10 am
ORD
-
SRQ
Nonstop3h 00m
United Airlines
Deal found 7/13$217
This United Airlines deal was found by Cheapflights users on 7/16. 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.
Sat 9/54:25 pm
SRQ
-
ORD
Nonstop3h 11m
United Airlines
Tue 9/811:10 am
ORD
-
SRQ
Nonstop2h 59m
United Airlines
Deal found 7/16$222
This United Airlines deal was found by Cheapflights users on 7/14. 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.
Wed 8/54:30 pm
SRQ
-
ORD
Nonstop3h 08m
United Airlines
Sat 8/811:10 am
ORD
-
SRQ
Nonstop3h 02m
United Airlines
Deal found 7/14$225
This United Airlines deal was found by Cheapflights users on 7/13. 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.
Wed 10/216:20 am
SRQ
-
ORD
1 stop6h 43m
United Airlines
Mon 10/2611:46 am
ORD
-
SRQ
Nonstop2h 54m
United Airlines
Deal found 7/13$227
This CheapOair deal was found by Cheapflights users on 7/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/58:45 am
SRQ
-
RFD
Nonstop2h 54m
Allegiant Air
Wed 8/1211:29 am
RFD
-
SRQ
Nonstop2h 45m
Allegiant Air
Deal found 7/13$229

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 July 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$98
(Mytrip)

One-way from

$60
(Kiwi.com)

Popular in

November

Cheapest in

August

Average price

$413

Good round-trip deal

$335 or less

Good one-way deal

$143 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. 5% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 18, 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 - RFD

SRQRFD

Sarasota Bradenton Intl

Sat 8/15

6:31 am-8:25 am

Nonstop2h 54m

Chicago Greater Rockford

Thu 8/27

11:54 am-3:34 pm

Nonstop2h 40m

$98

SarasotaChicago

SRQ - RFD

SRQRFD

Sarasota Bradenton Intl

Thu 9/17

9:15 am-11:05 am

Nonstop2h 50m

Chicago Greater Rockford

Sun 9/20

11:55 am-3:35 pm

Nonstop2h 40m

$137

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Wed 9/16

5:55 pm-7:35 pm

Nonstop2h 40m

Chicago Midway

Sat 9/19

7:45 am-2:40 pm

1 stop5h 55m

$227

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Thu 9/17

4:25 pm-6:35 pm

Nonstop3h 10m

Chicago O'Hare Intl

Thu 9/24

7:00 am-11:07 am

Nonstop3h 07m

$227

SarasotaChicago

SRQ - RFD

SRQRFD

Sarasota Bradenton Intl

Wed 8/5

8:45 am-10:39 am

Nonstop2h 54m

Chicago Greater Rockford

Wed 8/12

11:29 am-3:14 pm

Nonstop2h 45m

$229

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Wed 8/12

2:00 pm-8:55 pm

1 stop7h 55m

Chicago O'Hare Intl

Wed 8/19

8:05 am-3:49 pm

1 stop6h 44m

$237

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Fri 10/30

5:35 pm-11:51 pm

1 stop7h 16m

Chicago O'Hare Intl

Tue 11/3

1:26 pm-7:46 pm

1 stop5h 20m

$237

SarasotaChicago

SRQ - RFD

SRQRFD

Sarasota Bradenton Intl

Thu 9/10

10:46 am-8:52 am

2 stops23h 06m

Chicago Greater Rockford

Thu 9/17

11:55 am-3:35 pm

Nonstop2h 40m

$245

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Wed 8/12

7:15 am-12:05 pm

2 stops5h 50m

Chicago Midway

Wed 8/19

10:10 am-8:00 pm

2 stops8h 50m

$247

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Wed 9/16

6:05 am-12:59 pm

1 stop7h 54m

Chicago O'Hare Intl

Sat 9/19

1:30 pm-11:19 pm

1 stop8h 49m

$247

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/16

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 July.
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, September is the cheapest month in which you can book a flight from Sarasota to Chicago (average of $351). Flying from Sarasota to Chicago in January is currently the most expensive (average of $460). 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 July 18, 2026.

It’s typically best to fly out from Sarasota to Chicago in the evening. Doing so could potentially save you 37% on the flight price compared to flying at noon, which is usually more expensive.

Weekly flight availability from Sarasota to Chicago

Explore weekly flight availability from Sarasota to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 18, 2026.

The most flights from SRQ to CHI are scheduled on a Wednesday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).

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 88 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 July 11, 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. Tuesday at noon 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 July 18, 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
8.0
Very good
4,241 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
United Airlines
7.4
Good
10,006 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
American Airlines
7.1
Good
11,827 reviews
Southwest
8.0
Very good
4,241 reviews

Crew

8.6

Comfort

8.0

Food

7.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

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 40m. There are 1036 mi between Sarasota and Chicago. Most flights are nonstop.

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

    According to our current data, Allegiant Air ($120), Delta ($142), and Southwest ($199) offers the cheapest pricing from Sarasota to Chicago. Allegiant Air is 70% 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 ($118).

  • 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: United Airlines (81%), Envoy Air (75%), Emirates( 75%).

  • What are the cheapest flights from Sarasota to Chicago?

    Looking at all options, your cheapest flight can be booked for $118. While the most popular route (Sarasota Bradenton Intl - Chicago O'Hare Intl) can be booked for $227 on average, our data indicates $335 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, September is the cheapest month in which you can book a flight from Sarasota to Chicago (average of $351). Flying from Sarasota to Chicago in January is currently the most expensive (average of $460). 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
Valparaiso
Hammond
Saint Joseph
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 July 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$120Average$207FlexibilityNo cancel feeOn-time88%
DeltaCheapest$142Average$287FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$199Average$433FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$239Average$402FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$251Average$418FlexibilityNo cancel feeOn-time69%

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