SRQ - CHI

$119 Find Cheap Flights from Sarasota to Chicago - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Sarasota to Chicago departing on 9/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Sarasota to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Sarasota to Chicago, as well as popular online travel agencies
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$319
Typical prices: $596-$387
Southwest
Tue 8/11Sat 8/15
SRQ - MDW • 2 stops
Cheapest non-stop
$324
Typical prices: $533-$367
United Airlines
Wed 8/5Sat 8/8
SRQ - ORD • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Southwest free carry-on beats Frontier Basic Fare, which can limit seat choice.
For comfort, choose United Economy Plus or Frontier Premium Bundle upgrades.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $319 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest, United Airlines and others. Average duration is 2h 50m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 44% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $260 (round-trip)
Shortest trip • 4h 34m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 29% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 55% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Sarasota to Chicago (SRQ-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Sarasota to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Sarasota to Chicago

Tue, Aug 11 - Sat, Aug 15
Southwest Logo
7:15 am - 12:05 pm
SRQ
-
MDW
5h 50m
2 stops
Southwest Logo
9:20 am - 6:45 pm
MDW
-
SRQ
8h 25m
2 stops
$319Southwest
Thu, Aug 13 - Mon, Aug 17
United Airlines Logo
6:05 am - 11:59 am
SRQ
-
ORD
6h 54m
1 stop
United Airlines Logo
3:55 pm - 11:15 pm
ORD
-
SRQ
6h 20m
1 stop
$319United Airlines
Wed, Aug 5 - Tue, Aug 11
Delta Logo
6:00 am - 2:09 pm
SRQ
-
ORD
9h 09m
1 stop
Delta Logo
5:30 am - 12:55 pm
ORD
-
SRQ
6h 25m
1 stop
$321Delta
Wed, Aug 5 - Sat, Aug 8
United Airlines Logo
4:30 pm - 6:38 pm
SRQ
-
ORD
3h 08mnonstop
United Airlines Logo
11:10 am - 3:12 pm
ORD
-
SRQ
3h 02mnonstop
$324United Airlines
Tue, Jul 14 - Mon, Jul 27
Southwest Logo
11:20 am - 3:50 pm
SRQ
-
MDW
5h 30m
1 stop
Southwest Logo
2:10 pm - 5:50 pm
MDW
-
SRQ
2h 40mnonstop
$325Southwest
Sat, Jul 11 - Tue, Jul 14
United Airlines Logo
4:30 pm - 6:46 pm
SRQ
-
ORD
3h 16mnonstop
United Airlines Logo
11:10 am - 3:12 pm
ORD
-
SRQ
3h 02mnonstop
$325United Airlines
Tue, Jul 7 - Wed, Jul 15
Delta Logo
6:00 am - 10:05 am
SRQ
-
MDW
5h 05m
1 stop
Delta Logo
9:19 am - 12:45 am
MDW
-
SRQ
14h 26m
2 stops
$326Delta
Thu, Aug 6 - Thu, Aug 13
American Airlines Logo
12:05 pm - 4:48 pm
SRQ
-
ORD
5h 43m
1 stop
American Airlines Logo
5:05 am - 11:20 am
ORD
-
SRQ
5h 15m
1 stop
$337American Airlines
Sat, Jul 18 - Sat, Jul 25
Allegiant Air Logo
6:31 am - 8:15 am
SRQ
-
RFD
2h 44mnonstop
Allegiant Air Logo
12:58 pm - 11:38 pm
RFD
-
SRQ
33h 40m
2 stops
$347Allegiant Air
Sat, Aug 15 - Sun, Aug 16
Allegiant Air Logo
6:31 am - 8:25 am
SRQ
-
RFD
2h 54mnonstop
Allegiant Air Logo
11:37 am - 3:49 pm
RFD
-
SRQ
27h 12m
3 stops
$355Allegiant Air
Booking Insights

KAYAK's insights & trends for Sarasota to Chicago flights

Get data-powered insights and trends into flights from Sarasota to Chicago to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Sarasota to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Sarasota to Chicago departing in August.

What is the cheapest Sarasota to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Sarasota to Chicago costs $146 on the route between Sarasota (SRQ) and Chicago Greater Rockford Airport (RFD). Over the past month, this route was, on average, 44% cheaper than other Sarasota-Chicago routes. The most popular route is between Sarasota (SRQ) and Chicago O'Hare Intl Airport (ORD).

What’s the cheapest day of the week to fly from Sarasota to Chicago?

The average price of all round-trip flights from Sarasota to Chicago clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Chicago on a Saturday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Sarasota to Chicago. For your return ticket, we recommend flying on a Wednesday and avoiding Sundays for the best deals.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Sarasota to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Sarasota to Chicago is August, where tickets cost $58 (return) on average. On the other hand, the most expensive months are April and September, where the average cost of round-trip tickets is $237 and $184 respectively.

Can I save money by flying with a layover from Sarasota to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $386, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Sarasota to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Sarasota to Chicago, you should book around 4 weeks before departure, which saves you about 29% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Expert advice

Expert advice for your flight from Sarasota to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Frontier, United Airlines, ORD and MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Ramsey Qubein

Ramsey Qubein

Expert on SRQ

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.

Good to know

Low seasonFebruary
Cheapest flight$119
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Sarasota to Chicago Midway Airport

When to book flights from Sarasota to Chicago

Are your dates flexible? Find out the best times to travel from Sarasota to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Sarasota to Chicago

  • What is the cheapest flight from Sarasota to Chicago?

    In the last 5 days, the lowest price for a flight from Sarasota to Chicago was $119 for a one-way ticket and $319 for a round-trip.

  • Do I need a passport to fly between Sarasota and Chicago?

    No

  • Which airports will I be using when flying from Sarasota to Chicago?

    On your way to Chicago, you’ll fly out from Sarasota Bradenton Intl. You’ll be landing in one of Chicago’s 2 airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Sarasota to Chicago?

    American Airlines, and JetBlue offer inflight Wi-Fi service on the Sarasota to Chicago flight route.

  • Which aircraft models fly most regularly from Sarasota to Chicago?

    The Airbus A320-100/200 is the aircraft model that flies most regularly on the Sarasota to Chicago flight route.

  • Which airline alliances offer flights from Sarasota to Chicago?

    SkyTeam, oneworld, and Star Alliance are the airline alliances operating flights between Sarasota and Chicago, with SkyTeam being the most commonly used for this route.

  • On which days can I fly direct from Sarasota to Chicago?

    There are nonstop flights from Sarasota to Chicago on a daily basis.

  • Which is the best airline for flights from Sarasota to Chicago, Southwest or United Airlines?

    The two airlines most popular with KAYAK users for flights from Sarasota to Chicago are Southwest and United Airlines. With an average price for the route of $382 and an overall rating of 7.9, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $373 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Sarasota to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Sarasota to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Sarasota to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Sarasota is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Sarasota to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Sarasota with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Sarasota to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Sarasota up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Sarasota to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $226 or less one-way and $369 or less round-trip.

Prefer to fly direct from Sarasota to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Sarasota Bradenton Intl to Chicago.
Find which airlines fly direct from Sarasota Bradenton Intl Airport to Chicago, which days they fly and book direct flights.

Direct departures

Sarasota Bradenton Intl to Chicago

Monday

Southwest,United Airlines

Southwest,United Airlines

Tuesday

Southwest,United Airlines

Southwest,United Airlines

Wednesday

Allegiant Air,Southwest,United Airlines

Allegiant Air,Southwest, +1 more

Thursday

Southwest,United Airlines,Allegiant Air

Southwest,United Airlines, +1 more

Friday

Southwest,United Airlines

Southwest,United Airlines

Saturday

Allegiant Air,American Airlines,Southwest, +1 more

Allegiant Air,American Airlines, +2 more

Sunday

Southwest,United Airlines,Allegiant Air

Southwest,United Airlines, +1 more

See more direct flights

Direct returns

Chicago to Sarasota Bradenton Intl

Monday

Southwest,United Airlines

Southwest,United Airlines

Tuesday

Southwest,United Airlines

Southwest,United Airlines

Wednesday

Allegiant Air,Southwest,United Airlines

Allegiant Air,Southwest, +1 more

Thursday

Southwest,United Airlines,Allegiant Air

Southwest,United Airlines, +1 more

Friday

Southwest,United Airlines

Southwest,United Airlines

Saturday

Allegiant Air,American Airlines,Southwest, +1 more

Allegiant Air,American Airlines, +2 more

Sunday

Southwest,United Airlines,Allegiant Air

Southwest,United Airlines, +1 more

See more direct flights

Reviews of the top 3 airlines serving from Sarasota to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Sarasota to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Sarasota to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
SouthwestOverall score based on 4235 reviews
8.1Boarding
7.5Entertainment
7.0Food
8.6Crew
8.0Comfort
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

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

Information on your arrival and departure airports