Cheap Flight Deals From Sarasota (TPA) to Chicago (CHI) Starting at $40

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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.

Sat, Apr 1
TPA
Tampa Intl.
MDW
Midway Intl.
$148 One way, just found
$148
One way
just found
Frontier Airlines
Sat, Apr 1 - Sat, Apr 8
TPA
Tampa Intl.
MDW
Midway Intl.
$148 Roundtrip, just found
$148
Roundtrip
just found
Frontier Airlines
Fri, Mar 31
TPA
Tampa Intl.
ORD
O'Hare Intl.
$418 One way, just found
$418
One way
just found
Spirit Airlines
Fri, Mar 31 - Tue, Apr 11
TPA
Tampa Intl.
ORD
O'Hare Intl.
$418 Roundtrip, just found
$418
Roundtrip
just found
Spirit Airlines
Fri, Mar 31
SRQ
Sarasota-Bradenton Intl.
ORD
O'Hare Intl.
$602 One way, found 1 day ago
$602
One way
found 1 day ago
United
Fri, Mar 31 - Mon, Apr 10
SRQ
Sarasota-Bradenton Intl.
ORD
O'Hare Intl.
$602 Roundtrip, found 1 day ago
$602
Roundtrip
found 1 day ago
United
Sun, Apr 2 - Sat, Apr 8
SRQ
Sarasota-Bradenton Intl.
MDW
Midway Intl.
$645 Roundtrip, found 4 days ago
$645
Roundtrip
found 4 days ago
Delta

Airfares from $40 One Way, $80 Round Trip from Sarasota to Chicago

Prices starting at $80 for return flights and $40 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.

Thu, May 11
TPA
Tampa
ORD
Chicago
$40 One way, just found
$40
One way
just found
Spirit Airlines
Sat, May 6
TPA
Tampa
MDW
Chicago
$44 One way, just found
$44
One way
just found
Frontier Airlines
Wed, Apr 19
TPA
Tampa
ORD
Chicago
$79 One way, just found
$79
One way
just found
American Airlines
Thu, May 11 - Tue, May 16
TPA
Tampa
ORD
Chicago
$80 Roundtrip, just found
$80
Roundtrip
just found
Spirit Airlines
Wed, Apr 19
TPA
Tampa
ORD
Chicago
$99 One way, just found
$99
One way
just found
United
Thu, Apr 20
TPA
Tampa
ORD
Chicago
$100 One way, just found
$100
One way
just found
Delta
Wed, Apr 19 - Tue, May 2
TPA
Tampa
ORD
Chicago
$158 Roundtrip, found 3 hours ago
$158
Roundtrip
found 3 hours ago
American Airlines
Fri, Apr 28 - Mon, May 1
TPA
Tampa
ORD
Chicago
$178 Roundtrip, just found
$178
Roundtrip
just found
United
Tue, Apr 25 - Wed, Apr 26
SRQ
Sarasota
MDW
Chicago
$188 Roundtrip, found 17 hours ago
$188
Roundtrip
found 17 hours ago
Frontier Airlines
Tue, Apr 18 - Tue, May 2
SRQ
Sarasota
ORD
Chicago
$226 Roundtrip, found 20 hours ago
$226
Roundtrip
found 20 hours ago
American Airlines

Chicago economy flight packages

Aloft Chicago Downtown River North, a Marriott Hotel
3.5-star property

Aloft Chicago Downtown River North, a Marriott Hotel

4.6/10 (1,028 reviews)

May 26 - May 29

3 night stay

Tampa (TPA) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Price was $704, price is now $536 per person
per person
Loved this hotel. Why: Location: the location was phenomenal it was walking distance from the key places plenty to do in the area. They had a restaurant down in the lobby it was awesome. The restaurant had happy hour 3-6 which it worked great. Service: The service was good from them sending me an email prior to arriving because the elevators weren't working the had only one working. They accommodate their guests with options. They also let us checkout late it worked out perfectly because we didn't have to head to the airport until 1pm. I highly recommend this hotel/location.

Reviewed on Dec 23, 2022

Chicago Marriott Midway
3.5-star property

Chicago Marriott Midway

4.2/10 (638 reviews)

May 26 - May 29

3 night stay

Tampa (TPA) to Chicago (MDW)

Spirit Airlines • Roundtrip • Coach
Price was $602, price is now $521 per person
per person
Very clean, friendly staff I would definitely stay again!

Reviewed on Feb 15, 2021

Chicago Marriott at Medical District/UIC
3.5-star property

Chicago Marriott at Medical District/UIC

4.3/10 (940 reviews)

May 26 - May 29

3 night stay

Tampa (TPA) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Price was $686, price is now $598 per person
per person
Easy check in, accommodating staff. Clean facilities, spacious room, valet parking . This is a great place to stay for a night out in Chicago.

Reviewed on Dec 24, 2021

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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, LOT - Polish Airlines, Aer Lingus, Copa Airlines, Air New Zealand, United Airlines, Alaska Airlines, Qantas, Southwest Airlines, Royal Jordanian, SAS, ANA, Lufthansa, Spirit Airlines, Gulf Air, British Airways
Earliest Flight Arrival
12:05PM UTC
Latest Flight Arrival
12:25AM 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

Am I able to catch a flight from Sarasota to Chicago now?
Our Covid-19 Travel Advisor can answer all your queries about travel restrictions and quarantine requirements when traveling by plane from Sarasota to Chicago.
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
If I am not able to travel due to COVID-19, can I cancel my flight to Chicago?
We get that traveling right now has its challenges, so it’s good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Chicago have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you’ll quickly see what options are available. Our Customer Service Portal is the place to go for more information.
Are there flights to Chicago with flexible change policies?
In most cases you’ll have the option to reschedule your flight to Chicago without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the “no change fees” filter and book with confidence.
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.