SRQ - CHI

$144 Find Cheap Flights from Sarasota to Chicago - Compare and Save

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Everything you should know

Cheapest round-trip
$144
Typical prices: $329-$495
Allegiant Air
Mon 12/3Mon 12/10
SRQ - RFD • Non-stop
Cheapest one-way
$153
Typical prices: $188-$326
Sun Country Air
Tue 12/25
SRQ - ORD • 1 stop
Nonstop flights
You can fly direct with United Airlines, American Airlines and others. Average duration is 3h 13m.
Direct flights
+1
Direct flights
+1
Top routes
Cheapest • 38% average savings
Most popular
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 14 weeks in advance save around 49% compared to booking last minute.
Insights
Insights
When to travel
Cheapest • 17% price drop
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Cheapest • Avg $260 (round-trip)
Shortest trip • 4h 49m (one-way)
Insights
Insights
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Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Sarasota to Chicago (SRQ-CHI)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Sarasota to Chicago

Thu, Dec 3 - Thu, Dec 10
Allegiant Air Logo
11:00 am - 12:59 pmSRQ  Sarasota Bradenton Intl-RFD Chicago Greater Rockford
2h 59mnonstop
Allegiant Air Logo
1:49 pm - 5:34 pmRFD  Chicago Greater Rockford-SRQ Sarasota Bradenton Intl
2h 45mnonstop
$144Allegiant Air
Thu, Dec 10 - Sun, Dec 13
Allegiant Air Logo
11:00 am - 12:59 pmSRQ  Sarasota Bradenton Intl-RFD Chicago Greater Rockford
2h 59mnonstop
Allegiant Air Logo
1:49 pm - 5:34 pmRFD  Chicago Greater Rockford-SRQ Sarasota Bradenton Intl
2h 45mnonstop
$190Allegiant Air
Thu, Dec 3 - Thu, Dec 10
Multiple Airlines Logo
2:49 pm - 9:26 amSRQ  Sarasota Bradenton Intl-RFD Chicago Greater Rockford
19h 37m2 stops Louisville Intl Tampa
Multiple Airlines Logo
1:49 pm - 5:34 pmRFD  Chicago Greater Rockford-SRQ Sarasota Bradenton Intl
2h 45mnonstop
$266Multiple Airlines
Thu, Dec 3 - Sat, Dec 5
Southwest Logo
12:45 pm - 2:45 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
3h 00mnonstop
Southwest Logo
3:45 pm - 7:20 pmMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
2h 35mnonstop
$291Southwest
Thu, Nov 19 - Thu, Nov 26
United Airlines Logo
4:34 pm - 6:46 pmSRQ  Sarasota Bradenton Intl-ORD Chicago O'Hare Intl
3h 12mnonstop
United Airlines Logo
7:15 am - 11:12 amORD  Chicago O'Hare Intl-SRQ Sarasota Bradenton Intl
2h 57mnonstop
$291United Airlines
Thu, Dec 3 - Sat, Dec 5
American Airlines Logo
1:06 pm - 3:30 pmSRQ  Sarasota Bradenton Intl-ORD Chicago O'Hare Intl
3h 24mnonstop
American Airlines Logo
12:59 pm - 4:58 pmORD  Chicago O'Hare Intl-SRQ Sarasota Bradenton Intl
2h 59mnonstop
$291American Airlines
Thu, Dec 10 - Sat, Dec 12
American Airlines Logo
1:06 pm - 3:30 pmSRQ  Sarasota Bradenton Intl-ORD Chicago O'Hare Intl
3h 24mnonstop
American Airlines Logo
12:59 pm - 4:58 pmORD  Chicago O'Hare Intl-SRQ Sarasota Bradenton Intl
2h 59mnonstop
$291American Airlines
Thu, Dec 3 - Sat, Dec 5
Southwest Logo
12:45 pm - 2:45 pmSRQ  Sarasota Bradenton Intl-MDW Chicago Midway
3h 00mnonstop
Southwest Logo
7:50 am - 3:20 pmMDW  Chicago Midway-SRQ Sarasota Bradenton Intl
6h 30m1 stop Nashville Intl
$301Southwest
Thu, Nov 19 - Thu, Nov 26
United Airlines Logo
6:00 am - 1:54 pmSRQ  Sarasota Bradenton Intl-ORD Chicago O'Hare Intl
8h 54m1 stop Newark
United Airlines Logo
11:15 am - 3:10 pmORD  Chicago O'Hare Intl-SRQ Sarasota Bradenton Intl
2h 55mnonstop
$301United Airlines
Thu, Nov 19 - Thu, Nov 26
Delta Logo
2:19 pm - 8:49 pmSRQ  Sarasota Bradenton Intl-ORD Chicago O'Hare Intl
7h 30m1 stop Atlanta Hartsfield-Jackson
Delta Logo
8:00 am - 1:14 pmORD  Chicago O'Hare Intl-SRQ Sarasota Bradenton Intl
4h 14m1 stop Atlanta Hartsfield-Jackson
$311Delta
Booking Insights

Price, demand and travel trends for Sarasota to Chicago flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Sarasota to Chicago?

Round-trip flights from Sarasota to Chicago typically range from $329 to $495. The lowest price found in the past 5 days was $144, on Allegiant Air.

What is the cheapest Sarasota to Chicago flight route?

Sarasota (SRQ) to Chicago Greater Rockford Airport (RFD) is the cheapest Sarasota to Chicago route, averaging $207 round-trip. Other Sarasota to Chicago routes average $401, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Sarasota to Chicago?

Based on deals KAYAK users found in the last 12 months, Saturday is the cheapest day of the week to fly from Sarasota to Chicago. It’s 13% cheaper than the average day, while Sunday is the most expensive, with prices 14% higher.

What’s the cheapest month to fly from Sarasota to Chicago?

•August is the cheapest month to fly from Sarasota to Chicago at $331 round-trip.
•January ($510) and November ($503) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 54% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

When are flights from Sarasota to Chicago the cheapest?

Flights from Sarasota to Chicago are cheapest 14 weeks before departure. Booking in this window typically costs about 49% less than the average last-minute fare (within 2 weeks of the flight), based on KAYAK data.

Expert advice

Expert advice for your flight from Sarasota to Chicago

 
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Frontier, United Airlines, ORD and MDW

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Ramsey Qubein

Ramsey Qubein

Expert on SRQ

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Key details for Sarasota to Chicago flights

Low season

February

Cheapest flight

$144
Beat the crowds with an average 35% drop in travelers.
The most popular month to fly with an average 30% increase in travelers.
Round-trip flight from Sarasota to Chicago Greater Rockford Airport

When to book flights from Sarasota to Chicago

Are your dates flexible? Find out the best times to travel from Sarasota to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Sarasota to Chicago flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What are the earliest and latest flights from Sarasota to Chicago?

    These are the earliest and latest flight times available from Sarasota to Chicago:

    • Earliest: departs at 6:06 am and lands at 9:19 am
    • Latest: departs at 8:00 pm and lands at 11:13 pm.

    The flight takes about 3h 13m.

  • What cabin classes can I book on flights from Sarasota to Chicago?

    Two cabin classes are available on flights from Sarasota to Chicago:

    • Economy Class
    • First Class

  • How long is a flight from Sarasota to Chicago?

    A nonstop flight from Sarasota to Chicago takes 3h 13m, covering 1,040 miles.

  • Do I need a passport to fly from Sarasota to Chicago?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Sarasota to Chicago flight?

    Round-trip flights from Sarasota to Chicago range from $329 to $495, with an average of $399 over the past 12 months. Anything below $329 counts as a good deal.

  • How expensive are last-minute Sarasota to Chicago flights?

    Last-minute fares on this route (booked within two weeks of departure) run 51% above the $399 route average. Book 14 weeks before departure for the lowest fares.

  • How much can I save by taking a layover when flying from Sarasota to Chicago?

    On this route, layover flights are cheaper than nonstop options on average. Layover fares average $260 round-trip via Philadelphia (PHL), compared to $399 for nonstop.

  • What is the standard checked-bag allowance on flights from Sarasota to Chicago?

    There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $30–$100 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

  • How are flight departures from Sarasota to Chicago spread across the day?

    Afternoon is the busiest departure period on Sarasota to Chicago flights, with 67% of flights leaving in that window. Morning departures account for 17%, evening flights for 16%, and night flights for 0%.

  • Which airlines offer Wi-Fi on Sarasota to Chicago flights?

    Two airlines offer in-flight Wi-Fi on Sarasota to Chicago flights:

    • American Airlines
    • JetBlue

    Pricing varies by airline and fare class. Some plans are included with the ticket or loyalty program; others are paid add-ons priced by flight length.

  • How are flight prices from Sarasota to Chicago looking right now?

    One-way fares from Sarasota to Chicago are currently lower than usual. Average one-way flight prices are about $164, which is 31% below the typical average for this route.

  • What car rental options are available in Chicago?

    Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Chicago O'Hare Intl Airport (ORD) — daily rates averaging $64:

    • Routes Car & Truck Rentals
    • Europcar
    • Hertz
    • Ace
    • Dollar

    Near Chicago Midway Airport (MDW) — daily rates averaging $84:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

    Near Chicago Greater Rockford Airport (RFD) — daily rates averaging $81:

    • Alamo
    • Enterprise Rent-A-Car
    • Budget
    • Avis
    • National

  • Which airports can I use when flying from Sarasota to Chicago?

    Flights from Sarasota to Chicago usually depart from Sarasota Bradenton Intl (SRQ) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

  • Which airports do connecting flights from Sarasota to Chicago pass through?

    One-stop flights from Sarasota to Chicago most commonly connect through:

    • Atlanta Hartsfield-Jackson (ATL) - 45% of one-stop connections
    • Charlotte Douglas (CLT) - 36% of one-stop connections
    • Miami (MIA) - 12% of one-stop connections
    • Nashville Intl (BNA) - 2% of one-stop connections

  • Can I save money by using flexible dates for flights from Sarasota to Chicago?

    Yes. Flexible dates can save you up to 24% on flights from Sarasota to Chicago. Saturday is the cheapest departure day at $350 round-trip on average, while Sunday is the most expensive at $455, a difference of $105.

    Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • What airlines fly from Sarasota to Chicago?

    4 airlines operate flights between Sarasota and Chicago. The airlines offering nonstop flights on this route include:

    • United Airlines
    • American Airlines
    • Southwest
    • Allegiant Air

  • How much time can I save by choosing a different layover airport from Sarasota to Chicago?

    Flying via Nashville Intl (BNA) gives the shortest average 1-stop total travel time at 4h 49m, compared with 5h 15m via Atlanta Hartsfield-Jackson (ATL) and 5h 36m via Charlotte Douglas (CLT).

  • What is the time difference between Sarasota and Chicago?

    Chicago is 1 hour behind Sarasota (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Chicago?

    Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago on KAYAK.

  • Which airlines offer extra legroom and free seat selection on Sarasota to Chicago flights?

    Among airlines operating Sarasota to Chicago flights:

    • United Airlines: offers extra legroom; offers free seat selection
    • Southwest: offers free seat selection
    • American Airlines: offers extra legroom; offers free seat selection

    Extra legroom and free seat selection availability depends on fare class and route.

  • Which airlines include bags at no extra cost on Sarasota to Chicago flights?

    Here are some options for this route, based on selected ticket types and cabin classes:

    • United Airlines: a cabin bag and a checked bag in Economy Class
    • American Airlines: a cabin bag and a checked bag in Economy Class
    • Southwest: a cabin bag in Economy Class class

    Bag allowance can vary by ticket type, cabin class, route and airline, so always check the fare details before booking.

Your guide to booking Sarasota to Chicago flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Saturday departure and avoid flying on Sunday. On this route, Saturday flights average $350, about $105 less than Sunday fares (23% savings) based on the last 12 months.
  • For the best chance at a low fare, aim to book around 14 weeks before you fly. On this route, that window historically saves about 49% versus last-minute pricing (KAYAK booking data, last 12 months).
  • If you can choose when to travel, plan your Sarasota to Chicago trip for August. Fares historically average $331 round-trip in that month - typically $179 less than the most expensive month, which is January (based on the last 12 months).
  • If you have the time, taking a 1-stop flight through Philadelphia Airport (PHL) can be cheaper than flying direct. The cheapest layover option averages $260 round-trip on this route - about $139 less than direct flights (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel Chicago Midway Airport

Prefer to fly direct from Sarasota to Chicago?

 
Find which airlines fly direct from Sarasota Bradenton Intl Airport to Chicago, which days they fly and book direct flights.

Direct departures

Sarasota Bradenton Intl to Chicago

Monday

Allegiant Air,American Airlines,Southwest, +1 more

Allegiant Air,American Airlines, +2 more

Tuesday

Allegiant Air,American Airlines,Southwest, +1 more

Allegiant Air,American Airlines, +2 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

Allegiant Air,American Airlines,Southwest, +1 more

Allegiant Air,American Airlines, +2 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

Allegiant Air,American Airlines,Southwest, +1 more

Allegiant Air,American Airlines, +2 more

Sunday

Allegiant Air,American Airlines,Southwest, +1 more

Allegiant Air,American Airlines, +2 more

See more direct flights

Direct returns

Chicago to Sarasota Bradenton Intl

Monday

Allegiant Air,American Airlines,Southwest, +1 more

Allegiant Air,American Airlines, +2 more

Tuesday

Allegiant Air,American Airlines,Southwest, +1 more

Allegiant Air,American Airlines, +2 more

Wednesday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Thursday

Allegiant Air,American Airlines,Southwest, +1 more

Allegiant Air,American Airlines, +2 more

Friday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Saturday

Allegiant Air,American Airlines,Southwest, +1 more

Allegiant Air,American Airlines, +2 more

Sunday

Allegiant Air,American Airlines,Southwest, +1 more

Allegiant Air,American Airlines, +2 more

See more direct flights

More options for your flight from Sarasota to Chicago

Complete your trip to Chicago with a hotel stay or car rental