$101 Find Cheap Flights from Chicago to Siesta Key

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Siesta Key departing on 10/30. 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.
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1 adult, Economy

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Cheap Flights from Chicago to Siesta Key (CHI-SRQ)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Siesta Key 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 Chicago to Siesta Key

Thu, Nov 6 - Sun, Nov 9
Frontier Logo
8:26 am - 8:01 pmORD-SRQ
10h 35m1 stop
Frontier Logo
8:30 pm - 7:26 amSRQ-ORD
11h 56m1 stop
$233Frontier
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Fri, Nov 7 - Mon, Nov 10
Allegiant Air Logo
5:35 pm - 11:42 amMDW-SRQ
17h 07m1 stop
Allegiant Air Logo
7:31 am - 3:22 pmSRQ-MDW
8h 51m1 stop
$234Allegiant Air
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Fri, Sep 12 - Wed, Sep 17
Delta Logo
8:20 pm - 11:36 amORD-SRQ
14h 16m1 stop
Delta Logo
3:15 pm - 7:57 amSRQ-ORD
17h 42m1 stop
$273Delta
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Tue, Sep 16 - Wed, Sep 17
United Airlines Logo
11:22 am - 3:15 pmORD-SRQ
2h 53mnonstop
United Airlines Logo
4:37 pm - 6:41 pmSRQ-ORD
3h 04mnonstop
$277United Airlines
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Wed, Sep 24 - Wed, Oct 1
Southwest Logo
1:25 pm - 5:05 pmMDW-SRQ
2h 40mnonstop
Southwest Logo
7:30 am - 9:10 amSRQ-MDW
2h 40mnonstop
$277Southwest
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Sat, Sep 13 - Tue, Sep 16
Delta Logo
7:00 am - 11:04 pmORD-SRQ
15h 04m2 stops
Delta Logo
3:15 pm - 7:57 amSRQ-ORD
17h 42m1 stop
$278Delta
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Wed, Dec 3 - Sat, Dec 6
Southwest Logo
6:15 pm - 10:00 pmMDW-SRQ
2h 45mnonstop
Southwest Logo
5:30 am - 7:15 amSRQ-MDW
2h 45mnonstop
$283Southwest
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Tue, Dec 2 - Sat, Dec 6
American Airlines Logo
7:55 am - 11:40 amORD-SRQ
2h 45mnonstop
American Airlines Logo
12:57 pm - 3:11 pmSRQ-ORD
3h 14mnonstop
$283American Airlines
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Tue, Sep 16 - Wed, Sep 17
United Airlines Logo
2:20 pm - 11:06 pmORD-SRQ
7h 46m1 stop
United Airlines Logo
4:37 pm - 6:41 pmSRQ-ORD
3h 04mnonstop
$287United Airlines
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Wed, Dec 17 - Wed, Jan 7
American Airlines Logo
8:29 am - 12:17 pmORD-SRQ
2h 48mnonstop
American Airlines Logo
1:50 pm - 7:26 pmSRQ-ORD
6h 36m1 stop
$293American Airlines
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Good to know

Low seasonAugust
Cheapest flight$101
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Chicago O'Hare Airport to Sarasota

When to book flights from Chicago to Siesta Key

Are your dates flexible? Find out the best times to travel from Chicago to Siesta Key based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Siesta Key

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

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway, Chicago O'Hare Intl or Chicago Greater Rockford. Siesta Key does not have its own airport so you’ll be flying into nearby Sarasota Bradenton Intl airport, which is 8.8 mi away.

  • How long does a flight from Chicago to Siesta Key take?

    Direct flights cover the 1,040 miles separating Chicago and Siesta Key in about 2h 35m.

  • How many flights are there between Chicago and Siesta Key?

    5 direct flights run between Chicago and Siesta Key on a daily basis. On average, there are about 35 departures each week.

  • What’s the cheapest day of the week to fly between Chicago and Siesta Key?

    Consider leaving on a Thursday and avoid Fridays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Tuesdays and the most expensive ones on Wednesdays.

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

    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 Chicago to Siesta Key.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Siesta Key from Chicago 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 Chicago to Siesta Key?

    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 Siesta Key with an airline and back to Chicago with another airline.

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

    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 Siesta Key from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Siesta Key?

    In the last 72 hours, the cheapest one-way ticket between Chicago and Siesta Key found on KAYAK was with Frontier for $101. Frontier offered a round-trip connection from $233 and Allegiant Air from $234.

Top tips for finding cheap flights from Chicago to Siesta Key

  • There is no airport in Siesta Key. Instead, you’ll be flying into Sarasota Bradenton Intl Airport when flying between Chicago and Siesta Key.
  • The cheapest flight from Chicago to Siesta Key was found 46 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be October, November and December. The cheapest month to fly is January.

Reviews of the top 5 airlines serving Chicago to Siesta Key

 
Need help choosing which airline to fly with from Chicago to Siesta Key? 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 4246 reviews
8.6Crew
7.0Food
8.0Comfort
7.5Entertainment
8.1Boarding
Airline reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

10.0 ExcellentKevin, Jul 2025MDW - PUJ
Read more Southwest reviews

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

It is southwest seat was ok. Not the most comfortable seat

Plz don't take away free bags and free seating

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

It went well. Plane wasn't full. Will be great when assigned seating is in place

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

Mechanic delay in addition to a 2 hour change in takeoff time was frustrating.

Delayed due to thunderstorms and no in-flight service due to rough weather — both of which are out of Delta’s control. Flight was good overall.

The flight attendants in SLC were rude. I arrived 40 minutes early to gate. Ticket said I needed check in for seat assignments and tried check in and attendants said they weren’t doing it. And proceeded to never call me to give me a ticket so when time to board I received the very last seat. Please relay to employees to do their job better..,

On this flight I felt the food offering was not as complete as on previous flights. The tomato salad was a bit off and there was nothing additional such a bread or butter. The breakfast was only one option, so you either ate what they had or ate nothing. The crew was efficient, but most seemed frustrated throughout the flight. The flight arrived early and was obstacle-free, so I’m overall quite happy, but the shine in the rest of the experience just wasn’t there.

The seats got pretty uncomfortable pretty fast. The armrests are bigger than on other planes, so I had less room in the actual seat. My butt hurt by the end of the flight. :/ comfort was the primary issue. The crew were fantastic!

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

this crew didn't care much. bumping carts into seats more times than i care to remember

Everything was fine except the entertainment was not working for half of the flight.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline

2 hour delay due to late plane, wrong size plane causing overbooking, and people getting off and on the plane after boarding was completed.

Since you have to pay for overhead bags then they shouldn't be running out of space and asking individuals who paid to remove stuff from the overhead

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

I chose the seats when booked the flight and paid for them. However after checking in I found we were assigned different seats!

It was a no frills flight. Would have liked to be able to charge my device

Seats were extremely uncomfortable and it was very hot on the plane.

Everything you need to know for your flight from Chicago to Siesta Key

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