Chicago

$79+ 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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
SRQ — CHI
Jul 8 — Jul 151
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Cheapflights Tip: The best prices from Sarasota Bradenton Intl to Chicago are usually found in February or January, booked 45 days in advance, depart on a Friday or Wednesday and return on a Monday

Cheap 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 3, 2025.

Round-trip from

$266
(Mytrip)

One-way from

$79
(Mytrip)

Popular in

October

Cheapest in

February

Average price

$381

Good round-trip deal

$373 or less

Good one-way deal

$156 or less
From Sarasota Bradenton Intl to Chicago (CHI)
One-way flight from Sarasota Bradenton Intl to Chicago (CHI)
Highest demand for flights based on searches. 26% potential increase in price ($129 potential increase over avg. RT price).
Cheapest flight prices on average. 7% potential price decrease ($27 potential savings vs. average RT price).
Average for round-trip flights in July 2025
Price to beat on a round-trip flight from Sarasota Bradenton Intl to Chicago (CHI).
Price to beat on a one-way flight from Sarasota Bradenton Intl to Chicago (CHI).

Find 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 3, 2025.

This Sun Country Air deal was found by Cheapflights users on 7/3. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/265:04 pmSRQ - ORD
1 stop16h 16mSun Country Air
Sat 11/2910:00 amORD - SRQ
1 stop22h 55mSun Country Air
Deal found 7/3$265
This Mytrip deal was found by Cheapflights users on 7/2. 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.
Fri 8/112:30 pmSRQ - ORD
2 stops12h 23mMultiple Airlines
Fri 8/86:17 pmORD - SRQ
1 stop15h 58mMultiple Airlines
Deal found 7/2$266
This Southwest deal was found by Cheapflights users on 7/2. 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.
Thu 8/147:30 amSRQ - MDW
1 stop8h 20mSouthwest
Mon 8/181:45 pmMDW - SRQ
Nonstop2h 35mSouthwest
Deal found 7/2$267
This United Airlines deal was found by Cheapflights users on 7/1. 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.
Thu 8/286:00 amSRQ - ORD
1 stop6h 49mUnited Airlines
Mon 9/111:22 amORD - SRQ
Nonstop2h 53mUnited Airlines
Deal found 7/1$267
This Mytrip deal was found by Cheapflights users on 7/2. 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.
Fri 8/111:35 amSRQ - RFD
2 stops21h 37mAllegiant Air
Sat 8/211:03 amRFD - SRQ
Nonstop2h 39mAllegiant Air
Deal found 7/2$273
This Delta deal was found by Cheapflights users on 7/1. 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 9/163:15 pmSRQ - ORD
1 stop17h 42mDelta
Mon 9/226:00 amORD - SRQ
1 stop7h 13mDelta
Deal found 7/1$275
This Southwest deal was found by Cheapflights users on 7/1. 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.
Thu 8/217:00 amSRQ - ORD
2 stops10h 25mSouthwest
Tue 9/21:50 pmORD - SRQ
1 stop6h 20mSouthwest
Deal found 7/1$282
This Delta deal was found by Cheapflights users on 7/1. 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 8/97:01 amSRQ - MDW
1 stop5h 47mDelta
Mon 8/186:04 amMDW - SRQ
1 stop5h 09mDelta
Deal found 7/1$285
This Frontier deal was found by Cheapflights users on 7/2. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/168:30 pmSRQ - MDW
1 stop11h 50mFrontier
Sun 10/198:15 amMDW - SRQ
1 stop10h 16mFrontier
Deal found 7/2$296
This American Airlines deal was found by Cheapflights users on 7/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/511:51 amSRQ - ORD
1 stop5h 24mAmerican Airlines
Tue 12/98:29 amORD - SRQ
Nonstop2h 48mAmerican Airlines
Deal found 7/2$300
This Mytrip deal was found by Cheapflights users on 7/1. 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 8/98:01 amSRQ - RFD
Nonstop2h 53mMultiple Airlines
Sun 8/173:41 pmRFD - SRQ
3 stops22h 20mMultiple Airlines
Deal found 7/1$345

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 3, 2025.
Use the filters below to find and compare flights from Sarasota to Chicago that are best for you.

Fly from

Sarasota

Fly to

Chicago

Route

Depart

Return

Price

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Wed 11/26

5:04 pm-8:20 am

1 stop16h 16m

Chicago O'Hare Intl

Sat 11/29

10:00 am-9:55 am

1 stop22h 55m

$265

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Fri 8/1

12:30 pm-11:53 pm

2 stops12h 23m

Chicago O'Hare Intl

Fri 8/8

6:17 pm-11:15 am

1 stop15h 58m

$266

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Thu 8/14

7:30 am-2:50 pm

1 stop8h 20m

Chicago Midway

Mon 8/18

1:45 pm-5:20 pm

Nonstop2h 35m

$267

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Thu 8/28

6:00 am-11:49 am

1 stop6h 49m

Chicago O'Hare Intl

Tue 9/2

11:22 am-3:15 pm

Nonstop2h 53m

$267

SarasotaChicago

SRQ - RFD

SRQRFD

Sarasota Bradenton Intl

Fri 8/1

11:35 am-8:12 am

2 stops21h 37m

Chicago Greater Rockford

Sat 8/2

11:03 am-2:42 pm

Nonstop2h 39m

$273

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Tue 9/16

3:15 pm-7:57 am

1 stop17h 42m

Chicago O'Hare Intl

Tue 9/23

5:30 am-11:50 am

1 stop5h 20m

$275

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Thu 8/21

7:00 am-4:25 pm

2 stops10h 25m

Chicago O'Hare Intl

Tue 9/2

1:50 pm-9:10 pm

1 stop6h 20m

$282

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Sat 8/9

7:01 am-11:48 am

1 stop5h 47m

Chicago Midway

Mon 8/18

6:04 am-12:13 pm

1 stop5h 09m

$285

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Thu 10/16

8:30 pm-7:20 am

1 stop11h 50m

Chicago Midway

Sun 10/19

8:15 am-7:31 pm

1 stop10h 16m

$296

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Fri 12/5

11:51 am-4:15 pm

1 stop5h 24m

Chicago O'Hare Intl

Tue 12/9

8:29 am-12:17 pm

Nonstop2h 48m

$300

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 23 results
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The best insider tips for Sarasota to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Sarasota to Chicago trip
Airports
SRQ

Expect short security lines at SRQ, usually under 10 minutes, even during peak periods. Plan for 20 minutes just in case.

Read more about SRQby Brandon Schultz
ORD

Use the 'L' train for a quick, reliable trip from ORD to downtown Chicago, avoiding traffic delays.

Read more about ORDby Ramsey Qubein
MDW

The Orange Line 'L' train offers a direct, 30-minute ride from MDW to downtown Chicago.

Read more about MDWby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

Ramsey Qubein

Ramsey Qubein

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

Brandon Schultz

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

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

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

Use this chart to determine the optimal time to book a round-trip flight from Sarasota to Chicago. Price data was last updated on June 27, 2025.

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 45 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 $245). Flying from Sarasota to Chicago in March is currently the most expensive (average of $321). 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 3, 2025.

It’s typically best to fly out from Sarasota to Chicago in the evening. Doing so could potentially save you 63% on the flight price compared to flying at noon, which is usually more expensive.

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 June 29, 2025.

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

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 3, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United 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.

Entertainment

7.6

Crew

8.6

Food

7.0

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Entertainment

7.6

Crew

8.6

Food

7.0

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
8.0
Very good

Entertainment

7.6

Crew

8.6

Food

7.0

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Entertainment

7.6

Crew

8.6

Food

7.0

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Entertainment

7.6

Crew

8.6

Food

7.0

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Entertainment

7.6

Crew

8.6

Food

7.0

Comfort

8.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 5 outbound flights to Chicago per day. 6 airlines have flights to Chicago from Sarasota Bradenton Intl on a regular basis.

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

    According to our current data, Southwest ($267), United Airlines ($267), and Delta ($270) offers the cheapest pricing from Sarasota to Chicago. Southwest is 26% 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 ($88), Frontier ($110), and JetBlue ($127).

  • What are the most popular routes 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: SkyWest Airlines (100%), American Airlines (100%), Qatar Airways( 100%).

  • What are the cheapest flights from Sarasota to Chicago?

    Looking at all options, your cheapest flight can be booked for $158. While the most popular route (Sarasota Bradenton Intl - Chicago O'Hare Intl) can be booked for $257 on average our data indicates $961 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 $245). Flying from Sarasota to Chicago in March is currently the most expensive (average of $321). 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 Sarasota?

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

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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.

Top 6 airlines flying from Sarasota to Chicago

Discover the top 6 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 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$48Average$141FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$97Average$185FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$217Average$373FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$228Average$437FlexibilityNo cancel feeOn-time69%
DeltaCheapest$262Average$477FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$303Average$379FlexibilityNo cancel feeOn-time63%

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