
$82 Cheap flight deals from Chicago (CHI) to Siesta Key (SRQ)
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This Weekend's Flight Deals from Chicago to Siesta Key
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Airfares from $82 One Way, $159 Round Trip from Chicago to Siesta Key
Prices starting at $159 for return flights and $82 for one-way flights to Siesta Key were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Siesta Key economy flight packages

Legacy Hotel at IMG Academy
Sep 25 - Sep 29
Chicago (CHI) to Sarasota (SRQ)
Reviewed on Jun 13, 2025

Ocean Club Treasure Island Hotel
Sep 2 - Sep 9
Chicago (CHI) to Tampa (TPA)
Tampa (TPA) to Chicago (CHI)
Reviewed on Apr 29, 2025

Siesta Key packages with premium economy flights

Hotel Alba, Tapestry Collection by Hilton
Sep 20 - Sep 23
Chicago (MDW) to Sarasota (SRQ)
Reviewed on Jul 27, 2025

The Pointe Condos by Barsala
Sep 20 - Sep 23
Chicago (MDW) to Sarasota (SRQ)
Reviewed on Oct 25, 2022

The Westshore Grand, A Tribute Portfolio Hotel, Tampa
Sep 20 - Sep 23
Chicago (MDW) to Sarasota (SRQ)
Reviewed on Jun 22, 2025
Siesta Key first class flight packages


Ocean Club Treasure Island Hotel
Sep 6 - Sep 10
Chicago (ORD) to Tampa (TPA)
Tampa (TPA) to Chicago (ORD)
Reviewed on Apr 29, 2025

Wyndham Grand Clearwater Beach
Sep 6 - Sep 10
Chicago (ORD) to Tampa (TPA)
Tampa (TPA) to Chicago (ORD)
Reviewed on Jun 21, 2025
More About Flying To Siesta Key from Chicago
Route Information for Flights from Chicago to Siesta Key
Origin Airport IATA Code | CHI |
---|---|
Destination Airport IATA Code | SRQ |
Distance | 1052 mi |
Direct Flight Airlines | Air Canada, Emirates, Air New Zealand, United Airlines |
Earliest Flight Arrival | 7:10PM UTC |
Latest Flight Arrival | 7:10PM UTC |
Chicago to Siesta Key
If you are looking to get guaranteed low prices for Chicago to Siesta Key flights then Orbitz is the place to go. We use cutting edge mobile tools to find the best deals on air tickets and to keep you updated on delays and changes.
Get Package Savings by Booking Flights and Hotels at the Same Time
Using the Orbitz Matrix display, you can see how much you will save on flights from Chicago to Siesta Key if the discount fare is combined with a hotel. You can also look at hotel reviews, photos and maps of the area, so it will be convenient to make your budget travel plans.
Orbitz for Business Helps Corporations save Money
Orbitz can assist all businesses from the small to major corporations with discounts on flights from Chicago to Siesta Key. We fine- tune your needs for Chicago to Siesta Key flights and optimize your plans by assessing your business and coming up with ways for you to save on air tickets.
Using Online Check-In Makes Flying Simple
You can use the Orbitz website to check-in for your flights from Chicago to Siesta Key. You can also make changes to your schedule or even cancel a flight.
Flights from Chicago
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Siesta Key Airports
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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.