What are the cheapest airlines flying from Sarasota to Chicago round-trip?

According to our current data, Southwest ($267), United Airlines ($267), and Delta ($270) offers the cheapest pricing from Sarasota to Chicago. Southwest is 26% cheaper than the average price of flights available within the next 90 days to this destination.

What are the cheapest airlines to fly from Sarasota to Chicago one-way?

The cheapest airlines for a one-way flight from Sarasota to Chicago are Allegiant Air ($88), Frontier ($110), and JetBlue ($127).

How far ahead should I book a flight from Sarasota to Chicago?

The price you pay for your flight from Sarasota to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 45 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Sarasota to Chicago?

Currently, August is the cheapest month in which you can book a flight from Sarasota to Chicago (average of $245). Flying from Sarasota to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest day to fly from Sarasota to Chicago?

Travelers seeking maximum savings on their Sarasota to Chicago flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What are the most popular routes from Sarasota to Chicago?

Most travelers choose Sarasota Bradenton Intl - Chicago O'Hare Intl, Sarasota Bradenton Intl - Chicago Midway or Sarasota Bradenton Intl - Chicago Greater Rockford when deciding on the best route from Sarasota to Chicago.

What are the cheapest flights from Sarasota to Chicago?

Looking at all options, your cheapest flight can be booked for $158. While the most popular route (Sarasota Bradenton Intl - Chicago O'Hare Intl) can be booked for $257 on average our data indicates $961 when flying from Sarasota to Chicago.

What are the most reliable airlines from Sarasota to Chicago?

Before booking your flight to Chicago from Sarasota, check out the most reliable airlines to get you to your destination on time: SkyWest Airlines (100%), American Airlines (100%), Qatar Airways( 100%).

What are the most popular airlines that fly from Sarasota to Chicago?

American Airlines, Delta and Frontier are the most popular airlines when flying from Sarasota to Chicago.

What is the cheapest day to fly round-trip from Sarasota to Chicago?

Travelers have found that booking a Thursday departure is the best way to save up to 37% on the cost of booking your flights compared to booking on days of the week where this route is of high demand.

How far in advance should I book a flight from Sarasota to Chicago?

To save up to 152% on this flight, we recommend booking at least 46 days prior to travel. The price may fluctuate and will likely increase closer to your departure date. Users on Cheapflights have found tickets from Sarasota to Chicago from $117 1-2 weeks out and tickets from $526 for flights departing within the next 72 hours.

What is the cheapest month to fly from Sarasota to Chicago?

February is one of the best times of the year to fly to Chicago from Sarasota. Prices for February average $363 per person but you can even find prices for as low as $26. The most expensive prices can be found in the month of October. Opting for a February flight can save you 80% on your journey compared to booking in October

What is the cheapest time of day to fly from SRQ to CHI?

It’s typically best to fly out from Sarasota to Chicago in the evening. Doing so could potentially save you 63% on the flight price compared to flying at noon, which is usually more expensive.

What airport do you fly from for flights from Sarasota to Chicago?

For a flight from Sarasota to Chicago, you will be flying from Sarasota Bradenton Intl. Sarasota Bradenton Intl (SRQ) is just 4.3 mi from the center of the city. Sarasota Bradenton Intl is the only Sarasota airport and it handles 5 outbound flights to Chicago per day. 6 airlines have flights to Chicago from Sarasota Bradenton Intl on a regular basis.

Can I find deals for flights from Sarasota to Chicago that include hotel bookings?

Yes. In addition to deals on Sarasota to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Sarasota to Chicago?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Sarasota to Chicago.

Can I find deals for business class flights from Sarasota to Chicago?

Yes. Cheapflights offers flight deals from Sarasota to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$79+ Flights from Sarasota to Chicago

Round-trip from	$266 (Mytrip)
One-way from	$79 (Mytrip)
Popular in	October
Cheapest in	February
Average price	$381
Good round-trip deal	$373 or less
Good one-way deal	$156 or less

SRQ

Expect short security lines at SRQ, usually under 10 minutes, even during peak periods. Plan for 20 minutes just in case.

ORD

Use the 'L' train for a quick, reliable trip from ORD to downtown Chicago, avoiding traffic delays.

MDW

The Orange Line 'L' train offers a direct, 30-minute ride from MDW to downtown Chicago.

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$48	Average$141	FlexibilityNo cancel fee	On-time62%
Allegiant Air	Cheapest$97	Average$185	FlexibilityNo cancel fee	On-time88%
American Airlines	Cheapest$217	Average$373	FlexibilityNo cancel fee	On-time71%
United Airlines	Cheapest$228	Average$437	FlexibilityNo cancel fee	On-time69%
Delta	Cheapest$262	Average$477	FlexibilityNo cancel fee	On-timeN/A
Southwest	Cheapest$303	Average$379	FlexibilityNo cancel fee	On-time63%

$79+ Cheap flights from Sarasota (SRQ) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/11. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Sarasota to Chicago with Cheapflights

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Cheapflights Tip: The best prices from Sarasota Bradenton Intl to Chicago are usually found in February or January, booked 45 days in advance, depart on a Friday or Wednesday and return on a Monday

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Cheapest flights from Sarasota to ChicagoExplore the most affordable flight options available from Sarasota to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2025.

Explore the most affordable flight options available from Sarasota to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2025.

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The best insider tips for Sarasota to Chicago flights

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Best time to book a flight from Sarasota to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Sarasota with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Sarasota to Chicago

How far ahead should I book a flight from Sarasota to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Sarasota to Chicago. Price data was last updated on June 27, 2025.

What is the cheapest month to book a flight from Sarasota to Chicago?

What is the cheapest time of day to fly from SRQ to CHI?

Find hourly flight availability from Sarasota to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 3, 2025.

What is the cheapest day to fly from Sarasota to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Sarasota to Chicago. Price data was last updated on June 29, 2025.

Reviews of airlines servicing Chicago

Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Sarasota to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Sarasota to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

What airport do you fly from for flights from Sarasota to Chicago?

What are the cheapest airlines flying from Sarasota to Chicago round-trip?

What are the cheapest airlines to fly from Sarasota to Chicago one-way?

What are the most popular routes from Sarasota to Chicago?

What are the most reliable airlines from Sarasota to Chicago?

What are the cheapest flights from Sarasota to Chicago?

Can I find deals for flights from Sarasota to Chicago that include hotel bookings?

How can I find direct flights from Sarasota to Chicago?

Can I find deals for business class flights from Sarasota to Chicago?

What is the cheapest month to book a flight from Sarasota to Chicago?

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Cheapest flights from Sarasota to Chicago
Explore the most affordable flight options available from Sarasota to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 3, 2025.