$26 Cheap flight deals from Sarasota (TPA) to Chicago (CHI)

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This Weekend's Flight Deals from Sarasota to Chicago

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.

Fri, May 3 - Tue, May 7
TPA
Tampa Intl.
MDW
Midway Intl.
$96 Roundtrip, found 1 hour ago
$96
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, May 3 from Tampa Intl. to Midway Intl., returning Tue, May 7, priced at $96 found 1 hour ago
Sat, May 4 - Wed, May 8
TPA
Tampa Intl.
ORD
O'Hare Intl.
$149 Roundtrip, found 3 hours ago
$149
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Sat, May 4 from Tampa Intl. to O'Hare Intl., returning Wed, May 8, priced at $149 found 3 hours ago
Fri, May 3 - Sun, May 5
SRQ
Sarasota-Bradenton Intl.
MDW
Midway Intl.
$182 Roundtrip, found 2 days ago
$182
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, May 3 from Sarasota-Bradenton Intl. to Midway Intl., returning Sun, May 5, priced at $182 found 2 days ago
Sat, May 4 - Wed, May 15
SRQ
Sarasota-Bradenton Intl.
ORD
O'Hare Intl.
$382 Roundtrip, found 1 day ago
$382
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, May 4 from Sarasota-Bradenton Intl. to O'Hare Intl., returning Wed, May 15, priced at $382 found 1 day ago

Airfares from $26 One Way, $45 Round Trip from Sarasota to Chicago

Prices starting at $45 for return flights and $26 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, May 8 - Sat, May 18
TPA
Tampa
ORD
Chicago
$45 Roundtrip, found 6 hours ago
$45
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Wed, May 8 from Tampa to Chicago, returning Sat, May 18, priced at $45 found 6 hours ago
Tue, May 21 - Tue, May 28
TPA
Tampa
MDW
Chicago
$53 Roundtrip, found 3 days ago
$53
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, May 21 from Tampa to Chicago, returning Tue, May 28, priced at $53 found 3 days ago
Sat, Jun 15 - Tue, Jun 25
SRQ
Sarasota
ORD
Chicago
$170 Roundtrip, found 1 day ago
$170
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Jun 15 from Sarasota to Chicago, returning Tue, Jun 25, priced at $170 found 1 day ago
Tue, May 14 - Wed, May 15
TPA
Tampa
ORD
Chicago
$179 Roundtrip, found 9 hours ago
$179
Roundtrip
found 9 hours ago
Select United flight, departing Tue, May 14 from Tampa to Chicago, returning Wed, May 15, priced at $179 found 9 hours ago
Tue, May 14 - Wed, May 15
TPA
Tampa
ORD
Chicago
$179 Roundtrip, found 9 hours ago
$179
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, May 14 from Tampa to Chicago, returning Wed, May 15, priced at $179 found 9 hours ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago
4.5-star property

JW Marriott Chicago

9.2/10 Wonderful! (1,002 reviews)

Jun 7 - Jun 10

3 night stay

Tampa (TPA) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
Birthday weekend getaway/Mamas weekend away! My girl friend and I enjoyed our stay here. The customer service was amazing from the concierge to the bell hop and front desk staff. Loved having a drink at the hotel bar in the evening. Everything was top notch! I loved that our bartender knew so much about the area and different popular destinations from dining to attractions. Stayed on the fourth floor, and was impressed by the amount of privacy we had in our "hallway." Once exiting the elevator, I used my key card to open a door to another "hallway" that only had two rooms in it. So quaint, so quiet. Loved it! The beds are so comfortable! Would definitely stay here again.

Reviewed on Nov 10, 2023

DoubleTree by Hilton Chicago - Magnificent Mile
4.0-star property

DoubleTree by Hilton Chicago - Magnificent Mile

8.6/10 Excellent! (2,153 reviews)

Jun 7 - Jun 10

3 night stay

Tampa (TPA) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
The garage was dark and dengue. The room description said city view. All you could see is a block wall. Orbitz description said the hotel had room service. They don’t. Web Site said no charge for early check in. They charged us $25 The room walls must be thin. We heard people talking from other rooms and in the hall. Anytime a neighbor used the restroom we could hear the water. Basically we got no sleep.

Reviewed on Apr 7, 2024

Fairmont Chicago at Millennium Park Gold Experience
4.5-star property

Fairmont Chicago at Millennium Park Gold Experience

9.2/10 Wonderful! (95 reviews)

Jun 7 - Jun 10

3 night stay

Tampa (TPA) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
per person
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More About Flying To Chicago from Sarasota

Route Information for Flights from Sarasota to Chicago

Origin Airport IATA Code
TPA
Destination Airport IATA Code
CHI
Distance
1013 mi
Direct Flight Airlines
American Airlines, Qatar Airways, JAL, Air Canada, Austrian, Emirates, Copa Airlines, Swiss, Air New Zealand, United Airlines, Alaska Airlines, Qantas, Southwest Airlines, Royal Jordanian, ANA, Brussels Airlines, Lufthansa, Spirit Airlines, British Airways, Gulf Air
Earliest Flight Arrival
12:30PM UTC
Latest Flight Arrival
2:54AM UTC

Find Cheap Flights from Sarasota to Chicago

Sarasota Bradenton International Airport

The Sarasota Bradenton International Airport is located at 6000 Airport Circle, approximately five miles from downtown Sarasota. Nine airlines service the airport-Air Canada, Air France, AirTran Airways, Alitalia, Delta, JetBlue, KLM, US Airways and United Airlines. Orbitz.com can find you flights from Sarasota to any destination quickly. The website searches the flights available, making it easy for you to find sales and tickets with a low cost.

Parking and Transportation

If you need to leave your car at the airport while you travel, the long-term parking lot costs $12 per day. If you don't want to park your car, you can take a taxi to the airport. Cab fare has a $2.25 meter drop and costs $2.15 per mile after that. Bus service is also available from downtown Sarasota to the airport. If you need a car when you arrive at your destination, you can reserve a rental car on Orbotiz.com. The website offers packages that include your flight and rental car. Purchasing the two services together will save you money.

Dining at the Airport

If you didn't have time to eat before your flight, you can grab a sandwich, salad or full meal at Dewar's Clubhouse. If you just need a quick snack, the airport also houses a Starbucks and a Dunkin' Donuts. When you use Orbitz.com to find flights from Sarasota, all of your travel arrangements are taken care of for you. Since you don't have anything to worry about, you'll have plenty of time to grab a bite to eat before you board your plane.

Airports in Chicago

Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.

Transportation from the Airport

Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.

Weather in Chicago

Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions

Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.

Frequently asked questions

Are there non-stop flights from Sarasota to Chicago?
Yes, a stress-free, direct flight from Tampa Airport to O’Hare Intl. Airport (ORD) is possible. At least 5 airlines operate nonstop services on this route, which means you can select the one that meets your travel needs. Check out the deals from these well-known carriers:

  • United Airlines
  • American Airlines
  • Spirit Airlines
  • Frontier Airlines
  • Southwest Airlines

What is the shortest flight from Sarasota to Chicago?
Flying from SRQ to Chicago, IL (ORD-O’Hare Intl.) will take you at least 3 hours and 25 minutes. Savor a wine and watch a movie or two — it’s the perfect opportunity to sit back and chill out.
What airlines fly from Sarasota to Chicago most frequently?
Here are the airlines that offer the most frequent flights between Sarasota and Chicago. Discover which one fits your travel plans: United Airlines - (UA) with 112 flights every month American Airlines - (AA) with 65 flights every month Spirit Airlines - (NK) with 30 flights every month Frontier Airlines - (F9) with 21 flights every month
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won’t keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

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.