SRQ - CHI

$131 Find Cheap Flights from Sarasota to Chicago

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 3/1. 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
Travelers love KAYAK
41 299 237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$284
Typical prices: $268-$439
Multiple Airlines
Mon 4/13Thu 4/30
SRQ - ORD • 2 stops
Cheapest non-stop
$302
Typical prices: $97-$135
Allegiant Air
Thu 4/2Sun 4/5
SRQ - RFD • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
United's Economy Plus offers extra legroom on this route.
MDW's Orange Line provides a quick ride to downtown.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Allegiant Air
Cheapest • from $302 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
SRQ
-
RFD
Cheapest • 29% average savings
SRQ
-
ORD
Most popular
Insights
Insights
Insights
Insights
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 34% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
February
Cheapest • 64% price drop
March
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
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

Mon, Apr 13 - Thu, Apr 30
Multiple Airlines Logo
6:35 pm - 9:17 pm
SRQ
-
ORD
27h 42m
2 stops
Multiple Airlines Logo
1:12 pm - 6:56 pm
ORD
-
SRQ
28h 44m
1 stop
$284Multiple Airlines
Thu, Apr 2 - Sun, Apr 5
Allegiant Air Logo
2:49 pm - 4:49 pm
SRQ
-
RFD
3h 00mnonstop
Allegiant Air Logo
5:42 pm - 9:22 pm
RFD
-
SRQ
2h 40mnonstop
$302Allegiant Air
Mon, Apr 13 - Thu, Apr 30
Multiple Airlines Logo
7:05 am - 6:40 pm
SRQ
-
ORD
12h 35m
1 stop
Multiple Airlines Logo
1:12 pm - 6:56 pm
ORD
-
SRQ
28h 44m
1 stop
$309Multiple Airlines
Tue, Feb 24 - Tue, Mar 3
Southwest Logo
12:30 pm - 7:00 pm
SRQ
-
MDW
7h 30m
1 stop
Southwest Logo
5:35 pm - 9:15 pm
MDW
-
SRQ
2h 40mnonstop
$329Southwest
Tue, Feb 17 - Tue, Feb 24
JetBlue Logo
9:01 pm - 11:26 pm
SRQ
-
ORD
27h 25m
1 stop
JetBlue Logo
6:04 am - 3:44 pm
ORD
-
SRQ
8h 40m
1 stop
$335JetBlue
Fri, Feb 20 - Sun, Feb 22
Southwest Logo
6:10 pm - 8:00 pm
SRQ
-
MDW
2h 50mnonstop
Southwest Logo
7:40 pm - 11:20 pm
MDW
-
SRQ
2h 40mnonstop
$337Southwest
Wed, Feb 18 - Mon, Feb 23
American Airlines Logo
5:45 pm - 8:00 pm
SRQ
-
ORD
3h 15mnonstop
American Airlines Logo
8:05 am - 11:56 am
ORD
-
SRQ
2h 51mnonstop
$337American Airlines
Thu, Mar 5 - Mon, Mar 9
United Airlines Logo
7:15 am - 9:34 am
SRQ
-
ORD
3h 19mnonstop
United Airlines Logo
4:14 pm - 8:07 pm
ORD
-
SRQ
2h 53mnonstop
$343United Airlines
Wed, Feb 18 - Mon, Feb 23
American Airlines Logo
5:45 pm - 8:00 pm
SRQ
-
ORD
3h 15mnonstop
American Airlines Logo
3:16 pm - 10:34 pm
ORD
-
SRQ
6h 18m
1 stop
$347American Airlines
Thu, Feb 12 - Sun, Feb 22
JetBlue Logo
5:10 pm - 11:26 pm
SRQ
-
ORD
7h 16m
1 stop
JetBlue Logo
6:04 am - 4:14 pm
ORD
-
SRQ
9h 10m
1 stop
$348JetBlue
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.

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 $139 on the route between Sarasota (SRQ) and Chicago Greater Rockford Airport (RFD). Over the past month, this route was, on average, 29% 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 Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday 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 February, where tickets cost $129 (return) on average. On the other hand, the most expensive months are November and January, where the average cost of round-trip tickets is $528 and $443 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 $347, 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 3 weeks before departure, which saves you about 34% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 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
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.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines, Frontier, 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.

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 seasonNovember
Cheapest flight$131
Best time to beat the crowds but there is an average 47% increase in price.
Most popular time to fly and prices are also 17% lower on average.
Flight from Sarasota to Chicago O'Hare 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 3 days, the lowest price for a flight from Sarasota to Chicago was $131 for a one-way ticket and $284 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?

    Only American Airlines offers 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 $377 and an overall rating of 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $412 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 $187 or less one-way and $288 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

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Tuesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Wednesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Thursday

Allegiant Air, American Airlines, Southwest, +1 more

Allegiant Air, American Airlines, +2 more

Friday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Saturday

American Airlines, Southwest, United Airlines, +1 more

American Airlines, Southwest, +2 more

Sunday

Allegiant Air, American Airlines, Southwest, +1 more

Allegiant Air, American Airlines, +2 more

See more direct flights

Direct returns

Chicago to Sarasota Bradenton Intl

Monday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Tuesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Wednesday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Thursday

Allegiant Air, American Airlines, Southwest, +1 more

Allegiant Air, American Airlines, +2 more

Friday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 more

Saturday

American Airlines, Southwest, United Airlines, +1 more

American Airlines, Southwest, +2 more

Sunday

Allegiant Air, American Airlines, Southwest, +1 more

Allegiant Air, American Airlines, +2 more

See more direct flights

Reviews of the top 4 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.
8.0
SouthwestOverall score based on 4268 reviews
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
7.0Food
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

The seats were comfortable, and the boarding process was pretty smooth.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

Flight got delayed for 5 hours no good explanation was offered ;(

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

The experience was good. No frills but I got there safe and sound and on time.

After boarding and un-boarding twice over 6+hours, the flight was canceled.

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

Information on your arrival and departure airports