Cheap flights from Sarasota (TPA) to Chicago (CHI)

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Lowest round trip fares by airline from Sarasota and Chicago

Cheapest prices ($33 One Way, $67 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in Chicago

Freehand Chicago

Freehand Chicago

3.5 out of 5
19 East Ohio Street, Chicago, IL, 60611
The price is $95 per night from Aug 29 to Aug 30
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and ...
4/5 Very Good! (1,003 reviews)
"The location."

Reviewed on Aug 4, 2022

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL, 60605
The price is $129 per night from Aug 21 to Aug 22
Stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast, and a 24-hour front desk. Our guests praise the breakfast and the restaurant in ...
3.1/5 (1,168 reviews)
Pleased
"Every employee was courteous and efficient. Location was excellent. The only problem we had was the air conditioning wasn't as cool as we liked it, still comfortable though. Would definitely stay again."

Reviewed on Aug 7, 2022

Travelodge by Wyndham Downtown Chicago
Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave, Elk Grove Village, IL, 60007
The price is $55 per night from Aug 23 to Aug 24
Stay at this business-friendly motel in Elk Grove Village. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the ...
4/5 Very Good! (1,001 reviews)
"I looked at a lot of places before booking this one and ultimately did because of the excellent reviews. It did not disappoint. It was clean and the staff is friendly. Shout out to Olga. They got it down to a science. Hardwood floors. Cozy bed. Might I add they have HBO and Cinemax. One of the days ..."

Reviewed on Aug 9, 2022

Motel 6 Elk Grove Village, IL - O'Hare
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Fly From Sarasota to Chicago

Origin Sarasota
Destination Chicago
Number of Daily Flights 39
Earliest Flight Departure Date Aug 16
Latest Flight Departure Date Aug 16
Popular Airlines United Airlines

Cheap flights from Sarasota to Chicago

Are you ready to book your flight, but feeling nervous about paying too much if prices drop in a few days? Don't play the waiting game. Our Best Price Guarantee means if you see a better fare for the same flight, we'll give you the difference in CheapCash, plus $50 more in CheapCash, which you can use to save on your hotel reservation.

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Save Even More Time and Money With a Chicago Travel Package

Once your flights are booked, why start all over again searching for a cheap hotel? Book your flight and hotel together, and save yourself more than time and energy. You'll also be able to take advantage of discounts and coupons on your Chicago vacation that you can't get when you book flights and hotel separately.

Relax in Chicago With Confidence and Convenience

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.