SRQ - CHI

$112 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 1/12. 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

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Everything you should know

Cheapest round-trip
$185
Allegiant Air
Thu 1/29Sun 2/1
SRQ - RFD • Non-stop
Cheapest one-way
$112
Typical prices: $162-$259
Multiple Airlines
Mon 1/12
SRQ - ORD • 2 stops
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 $185 (round-trip)
Southwest
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
SRQ-RFD
Cheapest • 37% average savings
SRQ-ORD
Most popular
Insights
Insights
Insights
Insights
When to book
2 weeks
in advance
Our data shows that travelers who book at least 2 weeks in advance save around 40% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
February
Cheapest • 67% 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

Thu, Jan 29 - Sun, Feb 1
Allegiant Air Logo
7:01 am - 9:02 am
SRQ
-
RFD
3h 01mnonstop
Allegiant Air Logo
9:52 am - 1:39 pm
RFD
-
SRQ
2h 47mnonstop
$185Allegiant Air
Mon, Dec 22 - Fri, Jan 2
Frontier Logo
3:08 pm - 8:06 pm
SRQ
-
ORD
5h 58m1 stop
Frontier Logo
5:15 am - 2:13 pm
ORD
-
SRQ
7h 58m1 stop
$224Frontier
Sun, Dec 21 - Fri, Jan 2
Allegiant Air Logo
8:01 am - 9:55 am
SRQ
-
RFD
2h 54mnonstop
Allegiant Air Logo
7:08 pm - 10:50 pm
RFD
-
SRQ
2h 42mnonstop
$226Allegiant Air
Fri, Jan 16 - Mon, Jan 19
Multiple Airlines Logo
7:05 am - 12:08 pm
SRQ
-
ORD
30h 03m2 stops
Multiple Airlines Logo
7:45 am - 4:37 pm
ORD
-
SRQ
7h 52m1 stop
$259Multiple Airlines
Thu, Jan 29 - Sun, Feb 1
Multiple Airlines Logo
7:31 am - 10:35 am
SRQ
-
ORD
28h 04m2 stops
Multiple Airlines Logo
5:25 am - 9:22 pm
ORD
-
SRQ
14h 57m1 stop
$262Multiple Airlines
Fri, Jan 16 - Tue, Jan 20
Delta Logo
7:30 pm - 7:58 am
SRQ
-
ORD
13h 28m1 stop
Delta Logo
6:00 am - 6:17 pm
ORD
-
SRQ
11h 17m1 stop
$265Delta
Fri, Jan 30 - Tue, Feb 3
JetBlue Logo
5:38 pm - 7:36 pm
SRQ
-
ORD
26h 58m1 stop
JetBlue Logo
9:40 am - 3:42 pm
ORD
-
SRQ
29h 02m1 stop
$266JetBlue
Sun, Jan 18 - Tue, Jan 20
Delta Logo
6:00 am - 5:45 pm
SRQ
-
ORD
12h 45m2 stops
Delta Logo
6:00 am - 6:17 pm
ORD
-
SRQ
11h 17m1 stop
$270Delta
Mon, Jan 12 - Wed, Jan 14
Southwest Logo
12:35 pm - 2:30 pm
SRQ
-
MDW
2h 55mnonstop
Southwest Logo
5:35 pm - 9:15 pm
MDW
-
SRQ
2h 40mnonstop
$331Southwest
Mon, Jan 12 - Wed, Jan 14
Southwest Logo
6:50 am - 11:35 am
SRQ
-
MDW
5h 45m1 stop
Southwest Logo
5:35 pm - 9:15 pm
MDW
-
SRQ
2h 40mnonstop
$341Southwest
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 $162 on the route between Sarasota (SRQ) and Chicago Greater Rockford Airport (RFD). Over the past month, this route was, on average, 37% 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 Friday 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 November and July, where the average cost of round-trip tickets is $528 and $411 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 $375 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 2 weeks before departure, which saves you about 40% 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.
Airlines
Southwest

Southwest's free carry-on policy includes a personal item.


Southwest offers free snacks and soft drinks on board.

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.

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.

American Airlines

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


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

Airports
SRQ

SRQ's small terminal makes navigation quick, but expect crowded spaces during peak times. Fast, free Wi-Fi is available throughout.

ORD

Take the CTA Blue Line from ORD to downtown Chicago for a reliable 45-minute journey, avoiding traffic delays.

MDW

MDW's Orange Line offers a 25-30 minute ride to downtown Chicago, ideal for avoiding traffic.

Our travel experts
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
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines, Frontier, ORD and MDW

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
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
Ramsey Qubein

Ramsey Qubein

Expert on SRQ

Ramsey Qubein

Ramsey Qubein

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.

Read more

Good to know

Low seasonNovember
Cheapest flight$112
Best time to beat the crowds but there is an average 52% increase in price.
Most popular time to fly and prices are also 18% 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 $112 for a one-way ticket and $185 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 Boeing 737 MAX 8 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 $376 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 $390 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 $180 or less one-way and $409 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

Allegiant Air, American Airlines, Southwest, +1 more

Allegiant Air, American Airlines, +2 more

Saturday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 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

Allegiant Air, American Airlines, Southwest, +1 more

Allegiant Air, American Airlines, +2 more

Saturday

American Airlines, Southwest, United Airlines

American Airlines, Southwest, +1 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.
7.9
SouthwestOverall score based on 4252 reviews
7.0Food
8.0Comfort
8.6Crew
7.5Entertainment
8.1Boarding
Airline reviews

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.

2.0 MediocreCharity, Nov 2025
MSP - MDW
Read more Southwest reviews

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.

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

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.

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.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

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.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

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.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

My flight was delayed by two hours which made it so that I would miss my layover flight. I stood in line for customer service for over an hour and when I reached the agent she told me to scan a QR code and it'll give me options. I wasn't offered any help, guidance or compensation, only told that I have options but that I had to figure it all out myself. I was refunded part of the trip and had to buy an expensive same day ticket from another airline in order to get home. I will never fly Frontier again.

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

Information on your arrival and departure airports