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$51+ 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 7/16. Fares are subject to change and may not be available on all flights or dates of travel.
SRQ — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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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 June 12, 2025.

Round-trip from

$259
(Mytrip)

One-way from

$51
(Mytrip)

Popular in

October

Cheapest in

February

Average price

$387

Good round-trip deal

$373 or less

Good one-way deal

$169 or less
From Sarasota Bradenton Intl to Chicago (CHI)
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One-way flight from Sarasota Bradenton Intl to Chicago (CHI)
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Highest demand for flights based on searches. 26% potential increase in price ($132 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($28 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Price to beat on a round-trip flight from Sarasota Bradenton Intl to Chicago (CHI).
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Price to beat on a one-way flight from Sarasota Bradenton Intl to Chicago (CHI).
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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 June 12, 2025.

This Mytrip deal was found by Cheapflights users on 6/9. 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 7/1112:30 pmSRQ - ORD
1 stop10h 00mMultiple Airlines
Sun 7/135:05 amORD - SRQ
2 stops35h 10mMultiple Airlines
Deal found 6/9$259
This Sun Country Air deal was found by Cheapflights users on 6/10. 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.
Sat 12/2010:43 amSRQ - ORD
1 stop7h 07mSun Country Air
Wed 12/3111:45 amORD - SRQ
1 stop22h 05mSun Country Air
Deal found 6/10$295
This Mytrip deal was found by Cheapflights users on 6/11. 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 7/109:15 pmSRQ - MDW
1 stop13h 26mAllegiant Air
Mon 7/149:12 amMDW - SRQ
2 stops27h 08mAllegiant Air
Deal found 6/11$300
This United Airlines deal was found by Cheapflights users on 6/12. 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 8/74:13 pmSRQ - ORD
Nonstop3h 08mUnited Airlines
Mon 8/1111:14 amORD - SRQ
Nonstop2h 56mUnited Airlines
Deal found 6/12$303
This Mytrip deal was found by Cheapflights users on 6/11. 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 7/1712:20 pmSRQ - RFD
2 stops31h 59mAllegiant Air
Tue 7/2211:11 amRFD - SRQ
2 stops24h 24mAllegiant Air
Deal found 6/11$304
This Delta deal was found by Cheapflights users on 6/11. 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 9/37:00 amSRQ - MDW
1 stop15h 26mDelta
Wed 9/106:00 amMDW - SRQ
1 stop8h 58mDelta
Deal found 6/11$305
This Delta deal was found by Cheapflights users on 6/11. 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 9/37:00 amSRQ - ORD
1 stop13h 09mDelta
Wed 9/109:45 amORD - SRQ
1 stop8h 05mDelta
Deal found 6/11$305
This Southwest deal was found by Cheapflights users on 6/12. 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 8/75:50 pmSRQ - MDW
1 stop5h 35mSouthwest
Mon 8/111:45 pmMDW - SRQ
Nonstop2h 35mSouthwest
Deal found 6/12$313
This Southwest deal was found by Cheapflights users on 6/11. 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 9/47:00 amSRQ - ORD
1 stop5h 50mSouthwest
Mon 9/82:55 pmORD - SRQ
2 stops5h 55mSouthwest
Deal found 6/11$328
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Sat 7/2612:33 pmSRQ - ORD
Nonstop3h 12mAmerican Airlines
Sat 8/28:10 amORD - SRQ
Nonstop2h 53mAmerican Airlines
Deal found 6/11$336
This Mytrip deal was found by Cheapflights users on 6/10. 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 7/311:50 amSRQ - RFD
2 stops32h 29mMultiple Airlines
Thu 7/109:21 amRFD - SRQ
2 stops28h 42mMultiple Airlines
Deal found 6/10$377

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 June 12, 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

Fri 7/11

12:30 pm-9:30 pm

1 stop10h 00m

Chicago O'Hare Intl

Sun 7/13

5:05 am-5:15 pm

2 stops35h 10m

$259

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Thu 7/10

9:15 pm-9:41 am

1 stop13h 26m

Chicago Midway

Mon 7/14

9:12 am-1:20 pm

2 stops27h 08m

$300

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Thu 8/7

4:13 pm-6:21 pm

Nonstop3h 08m

Chicago O'Hare Intl

Mon 8/11

11:14 am-3:10 pm

Nonstop2h 56m

$303

SarasotaChicago

SRQ - RFD

SRQRFD

Sarasota Bradenton Intl

Thu 7/17

12:20 pm-7:19 pm

2 stops31h 59m

Chicago Greater Rockford

Tue 7/22

11:11 am-12:35 pm

2 stops24h 24m

$304

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Wed 9/3

7:00 am-9:26 pm

1 stop15h 26m

Chicago Midway

Wed 9/10

6:00 am-3:58 pm

1 stop8h 58m

$305

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Wed 9/3

7:00 am-7:09 pm

1 stop13h 09m

Chicago O'Hare Intl

Wed 9/10

9:45 am-6:50 pm

1 stop8h 05m

$305

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Thu 8/7

5:50 pm-10:25 pm

1 stop5h 35m

Chicago Midway

Mon 8/11

1:45 pm-5:20 pm

Nonstop2h 35m

$313

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Thu 9/4

7:00 am-11:50 am

1 stop5h 50m

Chicago O'Hare Intl

Mon 9/8

2:55 pm-9:50 pm

2 stops5h 55m

$328

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Sat 7/26

12:33 pm-2:45 pm

Nonstop3h 12m

Chicago O'Hare Intl

Sat 8/2

8:10 am-12:03 pm

Nonstop2h 53m

$336

SarasotaChicago

SRQ - RFD

SRQRFD

Sarasota Bradenton Intl

Thu 7/3

11:50 am-7:19 pm

2 stops32h 29m

Chicago Greater Rockford

Thu 7/10

9:21 am-3:03 pm

2 stops28h 42m

$377

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 22 results
1
2
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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 9, 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 June 12, 2025.

It’s typically best to fly out from Sarasota to Chicago in the evening. Doing so could potentially save you 65% 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 8, 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.

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 June 12, 2025.

The most flights from SRQ to CHI are scheduled on a Monday (6 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 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. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

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.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

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.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

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.
United Airlines
7.4
Good
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

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.
Allegiant Air
7.3
Good
725 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

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.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Crew

8.6

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, Allegiant Air ($300), United Airlines ($303), and Delta ($305) offers the cheapest pricing from Sarasota to Chicago. Allegiant Air is 17% 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 ($51), United Airlines ($122), and Sun Country Air ($143).

  • 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: SkyWest Airlines (100%), Frontier (78%), Qatar Airways( 77%).

  • 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 $233 on average our data indicates $853 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.
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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$48Average$127FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$97Average$185FlexibilityNo cancel feeOn-time88%
American AirlinesCheapest$217Average$371FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$218Average$430FlexibilityNo cancel feeOn-time69%
DeltaCheapest$262Average$480FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$303Average$379FlexibilityNo cancel feeOn-time63%

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