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Find cheap flights from Chicago to Siesta Key from $106

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 7/7. 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
0 bags
Fri 6/7
Fri 6/14

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Good to know

Low season

October

High season

March

Cheapest flight

$106
Best time to beat the crowds but there is an average 7% increase in price.
Most popular time to fly with an average 15% increase in price.
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 43m.

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

    10 direct flights run between Chicago and Siesta Key on a daily basis. On average, there are about 73 departures each week.

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

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

  • 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 $106. Frontier offered a round-trip connection from $158 and United Airlines from $235.

See more FAQs

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 34 days before departure, on average.
  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be November, December and January. The cheapest month to fly is April.
See more tips

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
DeltaOverall score based on 10793 reviews
8.6Crew
8.0Entertainment
7.4Food
7.9Comfort
8.2Boarding
Airline reviews

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

10.0 ExcellentDonnel, Apr 2024ATL - EYW
Read more about Delta reviews

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

They did a fine job. Can't wait to use Delta in the future.

Seat back monitors and outlets were dead and not working.

The experience was good and the flight departed on time and landed early

The flight was delayed but we got to our final destination.

public website still broken for years randomly blocking browsers with privacy options active after loading a page maybe once. check-in on laptop was almost impossible but eventually randomly worked. had to print pass at airport since couldn't get back in to load digital pass on mobile firefox or chrome. red eye flight so smooth onboarding, plenty of room to spread out, easy offboarding. onboard wifi instructions mention vpn can cause problems connecting but fails to also mention private dns. no printed or built in menu list, seems weird to require personal device to point at qr code link for menu which does not even allow direct ordering. people with health condition risk related dietary restrictions trying to avoid for example cholesterol and sugar are left guessing what they can order either way without nutritional info highlights (cranberry juice was minute maid cocktail with as much suger as typical can of soda). tap to pay wasn't working and always seems sketchy to manually enter card info. good movie variety, so limited tv was okay.

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

Boarding super slow with people allowed to linger in aisles

There were choices for the snacks. Good choices and tasty lunch and breakfast as well.

The net issue I had was with the gate agent. We had added a carryon to our boarding pass when we checked bags. When I got to the boarding gate the agent was rude asking why I had a backpack - I said I added it - even had an orange tag on it. She ripped my tag off and swung her monitor around to show me how she was right- saying it isn’t wasn’t listed - only a checked bag. I explained again that I wasn’t sure what the issue was but I wouldn’t have an orange tag if I hadn’t added it. Then she finally checked my husband’s boarding pass and found that the agent at checkin had added my carryon to his boarding pass instead of mine. She sent me on my way without my orange tag. Was a bit embarrassing for me the tone she used with me assuming I was trying to get away with something.

Gate agent asked if I could switch seats so a family could sit together. Agent moved me to a seat in the front of the plane, no charge. It was easy. The agent did a great job.

Great seat space. However food and drink prices outrageous. Jabbing to pay for a carry on bag or stuck paying at the gate too much.

Every Allegiant Air flight I've ever taken has been delayed. This flight was delayed a full 2 hours. It was excuse after excuse after excuse. It was a flight from southern Florida. They made us board the plane on time, but made us wait for 2 hours on the tarmac. Because the engines were kept shut off, so was the air conditioning. One can only imagine how hot the air was in the cabin over those 2 hours on the tarmac, while in the hot Florida sun. Just terrible.

Actually, for the price, I'm willing to put up with a little discomfort (upright chairs) and at times inconveniences (like any airline), lack of entertainment (I can bring my own). My flight was non stop and smooth. I would fly this route again.

The flight was delayed 6 hours and we were only offered an $8 food credit. My husband stood in line to get the credit for 45 minutes and when he got close to the end of the line the computers went down.

Worst ever! Flight cancelled supposedly for weather even though we k ow of many others who flew into Bangor same time no problem. At the airport there was no customer service at all just refund and no possibility of rebook for 3-4 days. Aweful won’t fly with them again!!

It’s a budget airline so adjust expectations accordingly. Nothing is without a fee but such is necessary for tickets to remain so affordable.

No complaints. It’s a budget airline so can’t expect any frills.

My TSA number was missing from my ticket which shouldn’t have happened since it’s in my file. The on board flight attendant who was a male, did not want to help me put my luggage in the overhead bin and made a very rude comment and was very unpleasant. The good… the woman who fixed my ticket with the TSA number was excellent and I had extra legroom which was perfect.

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Everything was good, hard to really comfortable on a flight that long.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight delayed 3 times, resulting in late arrival, rental car place gave car away resulting in increased BS charges because I was late. Frontier blows.

It was impossible to change a carry-on for a checked bag after the initial selection. The flight was delayed 14 hours "to allow for a late arriving aircraft." The seats were shockingly uncomfortable. This was only the second time I've seen seats that didn't recline in an airline. The first was in an East Bloc airline before the fall if the Iron Curtain.

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

First time flying Frontier, I am not sure the Ala Carte menu of options is for me.

I liked getting off the plane. Everything else was well below standards. Not even offering a bag of peanuts for free for a 4 hours flight is ridiculous.

There was no wifi, there was no usb charger on the planes Frontier lowered the weight limit on suitcases from 50 to 40 pounds Frontier now charges for a seat...really? If i don't pay for a basic seat, do i stand the whole flight? Frontier now charges for the carry on, just like for the checked suitcase The bundle pricing is way over priced.

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

Bought seats on the flight and they were supposed to be 2 and a jumpseat. Plane clearly changed and it was a regular 3 seat row. Asked for a refund and was denied. If I wanted to sit next to someone else I wouldn't have bought the seats..

Book cheap flights from Chicago to Siesta Key

Recent round-trip flight deals

6/11Tue
1 stopFrontier
7h 01mORD-SRQ
6/15Sat
1 stopFrontier
6h 09mSRQ-ORD
$158
6/8Sat
1 stopFrontier
10h 11mORD-SRQ
6/15Sat
1 stopFrontier
6h 09mSRQ-ORD
$166
8/3Sat
nonstopUnited Airlines
2h 53mORD-SRQ
8/10Sat
nonstopUnited Airlines
3h 01mSRQ-ORD
$235
8/3Sat
1 stopDelta
4h 57mORD-SRQ
8/10Sat
1 stopDelta
5h 44mSRQ-ORD
$254
8/3Sat
1 stopDelta
4h 55mMDW-SRQ
8/7Wed
1 stopDelta
5h 52mSRQ-MDW
$254
7/16Tue
1 stopAmerican Airlines
4h 50mORD-SRQ
7/23Tue
1 stopAmerican Airlines
5h 09mSRQ-ORD
$259
7/16Tue
2 stopsAmerican Airlines
6h 50mORD-SRQ
7/23Tue
1 stopAmerican Airlines
5h 09mSRQ-ORD
$265
6/6Thu
1 stop
16h 18mORD-SRQ
6/9Sun
2 stops
20h 41mSRQ-ORD
$289
6/6Thu
1 stop
16h 18mORD-SRQ
6/9Sun
2 stops
20h 41mSRQ-ORD
$291
8/3Sat
nonstopUnited Airlines
2h 53mORD-SRQ
8/10Sat
1 stopUnited Airlines
6h 58mSRQ-ORD
$322

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Recent one-way flight deals

7/7Sun
1 stopFrontier
9h 32mORD-SRQ
$106
6/29Sat
1 stopFrontier
10h 11mORD-SRQ
$111
6/6Thu
1 stop
16h 18mORD-SRQ
$119
7/9Tue
1 stopDelta
5h 37mMDW-SRQ
$131
10/9Wed
1 stopDelta
4h 32mMDW-SRQ
$132
5/30Thu
2 stops
26h 33mORD-SRQ
$135
7/6Sat
1 stopAmerican Airlines
6h 38mORD-SRQ
$156
6/4Tue
nonstopUnited Airlines
2h 53mORD-SRQ
$162
6/30Sun
1 stopAmerican Airlines
6h 01mORD-SRQ
$186
7/6Sat
nonstopUnited Airlines
2h 53mORD-SRQ
$188

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Last minute flights from Chicago to Siesta Key

Last minute flight, train and bus deals

5/9Thu
multi-stop
24h 21mORD-SRQ
5/13Mon
multi-stop
15h 34mSRQ-ORD
$506
5/9Thu
multi-stop
24h 21mORD-SRQ
5/13Mon
multi-stop
31h 35mSRQ-ORD
$511
5/9Thu
multi-stop
30h 19mORD-SRQ
5/13Mon
multi-stop
31h 35mSRQ-ORD
$567
5/13Mon
multi-stopAmerican Airlines
10h 15mORD-SRQ
5/25Sat
multi-stopAmerican Airlines
5h 38mSRQ-ORD
$598
5/13Mon
multi-stopUnited Airlines
7h 01mORD-SRQ
5/25Sat
nonstopUnited Airlines
3h 00mSRQ-ORD
$602
5/12Sun
nonstopUnited Airlines
2h 49mORD-SRQ
5/15Wed
multi-stopUnited Airlines
15h 35mSRQ-ORD
$671
5/13Mon
multi-stopAmerican Airlines
4h 35mORD-SRQ
5/25Sat
multi-stopAmerican Airlines
7h 14mSRQ-ORD
$679
5/11Sat
multi-stopDelta
7h 05mMDW-SRQ
5/18Sat
multi-stopDelta
6h 11mSRQ-MDW
$691
5/9Thu
multi-stopFrontier
7h 35mMDW-SRQ
5/10Fri
multi-stopFrontier
7h 23mSRQ-MDW
$717
5/13Mon
multi-stopDelta
8h 05mORD-SRQ
5/26Sun
multi-stopDelta
6h 19mSRQ-ORD
$792

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Flights to Siesta Key

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