SRQ - CHI

$142 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 4/9. 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
$210
Allegiant Air
Thu 4/9Thu 4/16
SRQ - RFD • Non-stop
Cheapest non-stop
$175
Allegiant Air
Sat 8/8Sat 8/15
SRQ - RFD • Non-stop
Advice from real travelers
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
Cheapest • from $175 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines, Southwest and others. Average duration is 3h 06m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 8% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $292 (round-trip)
Shortest trip • 4h 49m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 23% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 29% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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Flight Deals
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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

Thu, Apr 9 - Thu, Apr 16
Allegiant Air Logo
9:00 am - 11:00 am
SRQ
-
RFD
3h 00mnonstop
Allegiant Air Logo
11:50 am - 3:30 pm
RFD
-
SRQ
2h 40mnonstop
$210Allegiant Air
Wed, Apr 15 - Tue, Apr 21
United Airlines Logo
9:20 am - 11:33 am
SRQ
-
ORD
3h 13mnonstop
United Airlines Logo
11:00 am - 3:01 pm
ORD
-
SRQ
3h 01mnonstop
$217United Airlines
Wed, Apr 15 - Tue, Apr 21
United Airlines Logo
9:20 am - 11:33 am
SRQ
-
ORD
3h 13mnonstop
United Airlines Logo
3:35 pm - 11:59 pm
ORD
-
SRQ
7h 24m
1 stop
$227United Airlines
Wed, Apr 15 - Wed, Apr 22
American Airlines Logo
12:47 pm - 2:57 pm
SRQ
-
ORD
3h 10mnonstop
American Airlines Logo
7:59 pm - 11:47 pm
ORD
-
SRQ
2h 48mnonstop
$231American Airlines
Thu, May 7 - Tue, May 12
Southwest Logo
7:05 am - 8:55 am
SRQ
-
MDW
2h 50mnonstop
Southwest Logo
1:30 pm - 5:05 pm
MDW
-
SRQ
2h 35mnonstop
$233Southwest
Thu, May 7 - Tue, May 12
United Airlines Logo
9:05 am - 11:21 am
SRQ
-
ORD
3h 16mnonstop
United Airlines Logo
11:15 am - 3:18 pm
ORD
-
SRQ
3h 03mnonstop
$233United Airlines
Tue, May 12 - Tue, May 19
Southwest Logo
4:10 pm - 10:15 pm
SRQ
-
MDW
7h 05m
1 stop
Southwest Logo
6:00 am - 11:10 am
MDW
-
SRQ
4h 10m
1 stop
$237Southwest
Wed, Apr 15 - Tue, Apr 21
Southwest Logo
6:05 pm - 9:55 pm
SRQ
-
ORD
4h 50m
1 stop
Southwest Logo
1:35 pm - 9:40 pm
ORD
-
SRQ
7h 05m
1 stop
$237Southwest
Wed, May 6 - Sat, May 16
American Airlines Logo
8:46 am - 10:55 am
SRQ
-
ORD
3h 09mnonstop
American Airlines Logo
7:59 pm - 11:47 pm
ORD
-
SRQ
2h 48mnonstop
$240American Airlines
Thu, Apr 9 - Thu, Apr 16
Multiple Airlines Logo
9:00 am - 11:00 am
SRQ
-
RFD
3h 00mnonstop
Multiple Airlines Logo
10:37 am - 8:58 pm
RFD
-
SRQ
57h 21m
3 stops
$372Multiple Airlines
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 April.

What is the cheapest Sarasota to Chicago flight route?

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

The absolute cheapest return flight from Sarasota to Chicago costs $270 on the route between Sarasota (SRQ) and Chicago O'Hare Intl Airport (ORD). However, over the past month, flights between Sarasota (SRQ) and Chicago Greater Rockford Airport (RFD) were, on average, 8% 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 Friday, 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 Saturdays 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 $276 (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 $473 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $364 on average.

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 23% 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
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 seasonFebruary
Best time to beat the crowds with an average 4% drop in price.

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 $142 for a one-way ticket and $175 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 Delta offer inflight Wi-Fi service on the Sarasota to Chicago flight route.

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

    The Boeing 737-800 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 $383 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 $405 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 $185 or less one-way and $379 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, +1 more

American Airlines,Southwest, +2 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

Allegiant Air,American Airlines,Southwest, +1 more

Allegiant Air,American Airlines, +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, +1 more

American Airlines,Southwest, +2 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

Allegiant Air,American Airlines,Southwest, +1 more

Allegiant Air,American Airlines, +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 4318 reviews
8.0Comfort
7.0Food
8.6Crew
8.1Boarding
7.5Entertainment
Airline reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

Long layover between flights to Long Island from BWI - need better coordination between flights

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

An entire day of delays. Cost lots of money. Meals and a hotel.

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

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.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

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

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

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