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$87+ 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 6/6. Fares are subject to change and may not be available on all flights or dates of travel.
SRQ — CHI
Apr 20 — Apr 271
Sun 4/20
Sun 4/27
1 adult, Economy
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1. Tell us where you want to go

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2. Select your favorite providers

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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 April 15, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$100
(Mytrip)

One-way from

$87
(Mytrip)

Popular in

October

Cheapest in

February

Average price

$340

Good round-trip deal

$184 or less

Good one-way deal

$140 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.
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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. 28% potential increase in price ($145 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
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).
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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 April 15, 2025.

This Mytrip deal was found by Cheapflights users on 4/14. 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.
Sun 5/46:01 amSRQ - RFD
Nonstop2h 51mAllegiant Air
Wed 5/149:44 amRFD - SRQ
Nonstop2h 39mAllegiant Air
Deal found 4/14$100
This Cheapflightsfares deal was found by Cheapflights users on 4/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/184:54 pmSRQ - ORD
Nonstop3h 12mFrontier
Mon 4/2112:12 pmORD - SRQ
Nonstop2h 52mFrontier
Deal found 4/13$243
This Mytrip deal was found by Cheapflights users on 4/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/66:01 amSRQ - ORD
1 stop11h 24mMultiple Airlines
Sun 6/810:00 amORD - SRQ
2 stops29h 30mMultiple Airlines
Deal found 4/13$262
This United Airlines deal was found by Cheapflights users on 4/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1312:15 pmSRQ - ORD
Nonstop3h 10mUnited Airlines
Tue 5/207:15 amORD - SRQ
Nonstop2h 58mUnited Airlines
Deal found 4/15$269
This Delta deal was found by Cheapflights users on 4/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/308:00 amSRQ - ORD
1 stop7h 30mDelta
Tue 5/66:35 amORD - SRQ
1 stop6h 39mDelta
Deal found 4/14$283
This Mytrip deal was found by Cheapflights users on 4/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/69:07 amSRQ - MDW
1 stop5h 56mAllegiant Air
Sun 6/811:45 amMDW - SRQ
2 stops24h 45mAllegiant Air
Deal found 4/13$285
This Southwest deal was found by Cheapflights users on 4/14. 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.
Wed 6/256:45 pmSRQ - MDW
Nonstop2h 45mSouthwest
Tue 7/17:10 pmMDW - SRQ
Nonstop2h 40mSouthwest
Deal found 4/14$286
This Delta deal was found by Cheapflights users on 4/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/3010:46 amSRQ - MDW
1 stop6h 26mDelta
Mon 5/54:59 pmMDW - SRQ
1 stop6h 00mDelta
Deal found 4/14$300
This Southwest deal was found by Cheapflights users on 4/14. 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.
Wed 4/306:50 amSRQ - ORD
1 stop6h 00mSouthwest
Mon 5/51:50 pmORD - SRQ
2 stops8h 10mSouthwest
Deal found 4/14$305
This American Airlines deal was found by Cheapflights users on 4/14. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/292:49 pmSRQ - ORD
Nonstop3h 11mAmerican Airlines
Fri 5/95:00 amORD - SRQ
1 stop7h 08mAmerican Airlines
Deal found 4/14$307
This Sun Country Air deal was found by Cheapflights users on 4/14. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2511:41 amSRQ - ORD
1 stop7h 58mSun Country Air
Sun 4/278:15 amORD - SRQ
1 stop25h 34mSun Country Air
Deal found 4/14$325
This JetBlue deal was found by Cheapflights users on 4/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/912:34 pmSRQ - ORD
1 stop10h 20mJetBlue
Mon 5/128:45 amORD - SRQ
1 stop9h 22mJetBlue
Deal found 4/14$389

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 April 15, 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 - RFD

SRQRFD

Sarasota Bradenton Intl

Sun 5/4

6:01 am-7:52 am

Nonstop2h 51m

Chicago Greater Rockford

Wed 5/14

9:44 am-1:23 pm

Nonstop2h 39m

$100

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Fri 6/6

6:01 am-4:25 pm

1 stop11h 24m

Chicago O'Hare Intl

Sun 6/8

10:00 am-4:30 pm

2 stops29h 30m

$262

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Tue 5/13

12:15 pm-2:25 pm

Nonstop3h 10m

Chicago O'Hare Intl

Tue 5/20

7:15 am-11:13 am

Nonstop2h 58m

$269

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Wed 4/30

8:00 am-2:30 pm

1 stop7h 30m

Chicago O'Hare Intl

Tue 5/6

6:35 am-2:14 pm

1 stop6h 39m

$283

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Fri 6/6

9:07 am-2:03 pm

1 stop5h 56m

Chicago Midway

Sun 6/8

11:45 am-1:30 pm

2 stops24h 45m

$285

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Wed 6/25

6:45 pm-8:30 pm

Nonstop2h 45m

Chicago Midway

Tue 7/1

7:10 pm-10:50 pm

Nonstop2h 40m

$286

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Tue 5/13

6:00 am-9:40 am

1 stop4h 40m

Chicago Midway

Tue 5/20

6:00 am-11:32 am

1 stop4h 32m

$289

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Wed 4/30

6:50 am-11:50 am

1 stop6h 00m

Chicago O'Hare Intl

Mon 5/5

1:50 pm-11:00 pm

2 stops8h 10m

$305

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Tue 4/29

2:49 pm-5:00 pm

Nonstop3h 11m

Chicago O'Hare Intl

Fri 5/9

5:00 am-1:08 pm

1 stop7h 08m

$307

SarasotaChicago

SRQ - ORD

SRQORD

Sarasota Bradenton Intl

Fri 4/25

11:41 am-6:39 pm

1 stop7h 58m

Chicago O'Hare Intl

Sun 4/27

8:15 am-10:49 am

1 stop25h 34m

$325

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/15

Showing 1-10 of 24 results
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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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
MytripPrice 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 Mytrip to be most consistent on Cheapflights vs. Mytrip Users can find the same prices on Sarasota-Chicago flight deals on Cheapflights vs. Mytrip >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 Mytrip the most. Mytrip 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

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 April 11, 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 22 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 April 15, 2025.

It’s typically best to fly out from Sarasota to Chicago in the evening. Doing so could potentially save you 73% on the flight price compared to flying in the afternoon, 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 March 30, 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. Tuesday at noon 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 April 15, 2025.

The most flights from SRQ to CHI are scheduled on a Monday (13 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 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 April 15, 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
4,279 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Boarding

8.2

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
4,279 reviews
Southwest
8.0
Very good
4,279 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Boarding

8.2

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
7,917 reviews
Southwest
8.0
Very good
4,279 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Boarding

8.2

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
8,658 reviews
Southwest
8.0
Very good
4,279 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Boarding

8.2

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.
JetBlue
7.3
Good
2,926 reviews
Southwest
8.0
Very good
4,279 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Boarding

8.2

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
734 reviews
Southwest
8.0
Very good
4,279 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Boarding

8.2

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 8 outbound flights to Chicago per day. 5 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 ($100), Delta ($283), and Southwest ($286) offers the cheapest pricing from Sarasota to Chicago. Allegiant Air is 72% 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 ($93), Southwest ($135), and United Airlines ($135).

  • 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: American Airlines (72%), Air Canada (71%), Emirates( 70%).

  • What are the cheapest flights from Sarasota to Chicago?

    Looking at all options, your cheapest flight can be booked for $60. While the most popular route (Sarasota Bradenton Intl - Chicago O'Hare Intl) can be booked for $247 on average our data indicates $400 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
Hammond
Benton Harbor
Porter
Lansing
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 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 April 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$37Average$120FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$217Average$363FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$248Average$413FlexibilityNo cancel feeOn-time69%
DeltaCheapest$249Average$555FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$303Average$390FlexibilityNo cancel feeOn-time63%

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