SRQ - CHI

$100 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 6/11. 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

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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Expert advice
Useful Info
Flights Deals

Cheap Flight Deals 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.

Recent round-trip flight deals from Sarasota to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Sarasota to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Allegiant Air Logo
7:01 am - 8:54 amSRQ-RFD
2h 53mnonstop
Allegiant Air Logo
9:44 am - 1:23 pmRFD-SRQ
2h 39mnonstop
$112Allegiant Air
Find Deal
Wed, Jul 2 - Wed, Jul 9
Allegiant Air Logo
7:01 am - 8:54 amSRQ-RFD
2h 53mnonstop
Allegiant Air Logo
10:14 am - 1:53 pmRFD-SRQ
2h 39mnonstop
$125Allegiant Air
Find Deal
Wed, May 14 - Sat, May 17
Southwest Logo
7:30 am - 9:10 amSRQ-MDW
2h 40mnonstop
Southwest Logo
6:00 am - 11:20 amMDW-SRQ
4h 20m1 stop
$279Southwest
Find Deal
Tue, Sep 30 - Wed, Oct 8
Southwest Logo
7:30 am - 9:10 amSRQ-MDW
2h 40mnonstop
Southwest Logo
7:45 am - 4:35 pmMDW-SRQ
7h 50m2 stops
$284Southwest
Find Deal
Tue, Sep 30 - Wed, Oct 8
Delta Logo
6:00 am - 9:40 amSRQ-MDW
4h 40m1 stop
Delta Logo
4:15 pm - 11:20 pmMDW-SRQ
6h 05m1 stop
$289Delta
Find Deal
Wed, May 28 - Wed, Jun 4
Delta Logo
12:37 pm - 4:47 pmSRQ-ORD
5h 10m1 stop
Delta Logo
11:07 am - 7:29 pmORD-SRQ
7h 22m1 stop
$289Delta
Find Deal
Tue, May 20 - Wed, May 28
United Airlines Logo
10:36 am - 7:57 amSRQ-ORD
22h 21m2 stops
United Airlines Logo
11:10 am - 3:06 pmORD-SRQ
2h 56mnonstop
$337United Airlines
Find Deal
Fri, May 16 - Sat, May 17
United Airlines Logo
10:36 am - 6:10 pmSRQ-ORD
8h 34m1 stop
United Airlines Logo
7:15 am - 11:13 amORD-SRQ
2h 58mnonstop
$342United Airlines
Find Deal
Wed, May 14 - Tue, May 20
American Airlines Logo
11:52 am - 5:35 pmSRQ-ORD
6h 43m1 stop
American Airlines Logo
11:40 am - 7:14 pmORD-SRQ
6h 34m2 stops
$351American Airlines
Find Deal
Thu, Jun 12 - Wed, Jun 18
American Airlines Logo
12:33 pm - 2:45 pmSRQ-ORD
3h 12mnonstop
American Airlines Logo
8:10 am - 12:03 pmORD-SRQ
2h 53mnonstop
$355American Airlines
Find Deal
Sat, Jul 26 - Sat, Aug 2
Expert advice

Expert advice for your flight from Sarasota to Chicago

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
United Airlines

United's Economy Plus offers up to 6 inches more legroom than standard economy.


Check United's Wi-Fi coverage map before purchasing Wi-Fi for reliable connectivity.

Southwest

Enjoy two free checked bags up to 50 pounds each, ideal for family travel.


Use EarlyBird Check-In for a better boarding position, avoiding middle seats.

Read more about Southwestby Blane Bachelor
Frontier

Frontier's Premium Bundle includes priority boarding and extra legroom seats.


Avoid Basic Fare to prevent middle seats; consider Economy Bundle for seat selection.

Read more about Frontierby Stefanie Waldek
American Airlines

Main Cabin Extra offers early boarding and complimentary drinks, enhancing comfort.


Download the American Airlines app for in-flight entertainment access.

Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines and Frontier

Stefanie Waldek

Stefanie Waldek

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.

Read more
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor

Blane Bachelor

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.

Read more
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

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.

Read more
Useful Info

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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Sarasota to Chicago.

Our data shows that the cheapest route for a return flight from Sarasota to Chicago cost $97 and was between Sarasota (SRQ) and Chicago Greater Rockford Airport (RFD). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $97.

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, Saturday is the most expensive day to fly from Sarasota to Chicago. For your return ticket, we recommend flying on a Monday 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 $115 (return) on average. On the other hand, the most expensive months are October and November, where the average cost of round-trip tickets is $674 and $442 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 $645, 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. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.

Good to know

Low seasonJuly
High seasonMarch
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly and prices are also 13% lower on average.

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 $100 for a one-way ticket and $112 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, JetBlue, 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?

    Star Alliance is the only airline alliance operating flights between Sarasota and Chicago.

  • 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 Delta?

    The two airlines most popular with KAYAK users for flights from Sarasota to Chicago are Southwest and Delta. With an average price for the route of $384 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $442 and an overall rating of 8.0.

  • 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 $154 or less one-way and $326 or less round-trip.

Prefer to fly direct from Sarasota 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

Allegiant Air, Southwest, United Airlines

Allegiant Air, Southwest, +1 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

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

Allegiant Air, Southwest, United Airlines

Allegiant Air, Southwest, +1 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
See more direct flights

Top 5 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 4294 reviews
8.0Comfort
8.2Boarding
7.1Food
8.6Crew
7.6Entertainment
Airline reviews

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

6.0 GoodJennifer, Apr 2025FLL - RDU
Read more Southwest reviews

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

WiFi on the flight was not working. Thus, entertainment options were limited.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

I had a wonderful flight, but the only thing that annoyed me was how crowded TSA was. I still believe airports and all planes work together to bunch everyone together to drive up cost.

Easy to book and to get check in and get on and off.

Everything worked well. Crew was as entertaining as is possible on a plane flight. Southwest still has good legroom:

I like that it was on time and the staff was friendly.

Glad flight made it out. So many delays due to hurricane. everyone did a great job.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Flight left early and arrived early. the whole trip was excellent.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Everything was great. Great service, excellent communication, and early arrival

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Good and consistent Printer in lounge did not work for me :(

Great - This was the last flight before hurricane closures and did a quick turnaround to get the plane heading north. Much appreciated.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

They canceled our flight and left us stranded to figure it out

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Flight was delayed multiple times and I chose to switch to another flight that had a layover. I finally arrived 7 hours later than I was supposed to.

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

They switched my flight to Spirit, Never using Kayak again,

The flight itself was ok and the pilot was very communicative. However, our flight was delayed for almost 3 hours, the gate was changed 3 times and there was no communication as we were waiting. The flight staff was overall a little crabby...I understand as they probably had a long day but we all did.

Asked for a seat change to be w my wife at the gate they were great in sorting it out to make it happen

They cancelled the flight and did nothing. I should be compensated for my uber rides to and from airport. Not a good service by frontier or kayak.

The worst service , the agents from the counter are really bad . Poor customer service . They didnt help me to get in the flight . I was on line when they close the flight without telling and I couldn’t board the plane . I will like to get my money back ey back because it was their fault. Really bad management , bad manners, bad additud

The check in process was a mess for no reason. I spent an hour waiting in line trying to get them to print my boarding pass and as a result I missed my flight.

After waiting several minutes to be acknowledged by 3 employees on their phones, was told we had missed our flight because the doors were closed at that literal moment. Had they given any actual service or help while we were standing there we would have been on with time to spare. More than 10 people were turned away in this fashion claiming there was no way they could let us on the plane, even though it was still sitting connected to the terminal. After the desk agents let us know they didn't care about the situation we were forced to pay more than twice the price of our original tickets as no credits were given for the price of the "missed" flight. And the icing on the cake was after being treated poorly, fleeced for another few hundred dollars for new tickets? We waited on the next plane for 25 minutes passed the "doors closed" time, letting almost an extra dozen passengers on board. You're company has lazy, disinterested employees and your lack of any real help will ensure this was the first and last time we fly Frontier. Awful.

The seats were extremely hard and uncomfortable. It was disappointing even for a budget airline.

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

Information on your arrival and departure airports

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