Cheap flights from Sarasota to Chicago from $90
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Sarasota to Chicago departing on 8/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Delta flights from Sarasota to Chicago Midway Airport
Our best Delta deals on Sarasota to Chicago Midway Airport flight tickets
Southwest flights from Sarasota to Chicago Midway Airport
Our best Southwest deals on Sarasota to Chicago Midway Airport flight tickets
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How to get the cheapest flight ticket from Sarasota to Chicago Midway Airport
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Chicago Midway Airport?
The month of August is, on average, the cheapest month to fly to Chicago Midway Airport from Sarasota, with most prices found around $324. If you are unable to visit Chicago Midway Airport during the month of August, then departing from Sarasota during the month February is also very affordable. Most momondo users find prices during this month for around $325.
What is the cheapest day to depart on your flight to Chicago Midway Airport?
According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Sarasota. The lowest ticket price found for a Friday departure recently was $373. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Tuesday is the most expensive day to depart from Sarasota because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $457.
What is the cheapest time of day to depart on your flight to Chicago Midway Airport?
Flying to Chicago Midway Airport from Sarasota in the morning is the least expensive time of day to depart. momondo users have found prices as low as $395 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $607. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Sarasota Bradenton Intl to Chicago Midway flight route?
Fly from Sarasota Bradenton Intl to Chicago Midway for the best Sarasota Bradenton Intl - Chicago Midway flight prices
What cabin class options are available on Sarasota Bradenton Intl to Chicago Midway flights?
There are 1 cabin classes available to choose from on Sarasota Bradenton Intl to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
How have Sarasota to Chicago Midway Airport flight prices changed over time?
What is the cheapest airline that flies from Sarasota Bradenton Intl to Chicago Midway?
Allegiant Air, Southwest, and Delta are the most popular carriers operating from Sarasota Bradenton Intl to Chicago Midway
What airlines fly to Chicago Midway Airport?
Southwest, Frontier and Delta are the top three most popular airlines that fly to Chicago Midway Airport from Sarasota according to our data. Southwest is the first choice among our users, with 50% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 5 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.
How many flights depart from Sarasota to Chicago Midway Airport on average per day?
As of June 2025, there are 2 flights per day flying from Sarasota to Chicago Midway Airport. The most common time of day flights depart is 6:00AM, with 37% of flights taking off at noon.
How many flights depart from Sarasota to Chicago Midway Airport on average per week?
As of June 2025, there are 16 flights per week flying from Sarasota to Chicago Midway Airport. The most common day of the week flights depart is Mon, with 19% of flights taking off on this day.
When to book flights from Sarasota to Chicago Midway Airport
Cheap Sarasota to Chicago Midway Airport (SRQ to MDW) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Sarasota to Chicago Midway Airport
How far is Sarasota Bradenton Intl to Chicago Midway by plane?
The straight-line distance from Sarasota Bradenton Intl to Chicago Midway is 1040.3 mi. Flights usually cover this in 2h 40m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Sarasota Bradenton Intl Airport to Chicago Midway Airport?
Prices for flights from Sarasota Bradenton Intl Airport to Chicago Midway Airport are refreshed on a daily basis.
How many operators does momondo search for flights from Sarasota Bradenton Intl Airport to Chicago Midway Airport?
There are 2 operators available for flights from Sarasota Bradenton Intl Airport to Chicago Midway Airport as of June 2025.
How old do you have to be to fly from Sarasota Bradenton Intl Airport to Chicago Midway Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Sarasota Bradenton Intl Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The required travel and health documents for your Chicago Midway Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago Midway Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Sarasota to Chicago Midway Airport?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Sarasota to Chicago Midway Airport is Boeing 737-800 Passenger/BBJ2 (winglets) (20.06% of total bookings). The next most popular plane models are Boeing 737-700 Passenger/BBJ1 (winglets) (13.17%), Boeing 737-800 (12.23%), and Boeing 737-700 (9.09%).
What is the most popular airline from Sarasota to Chicago Midway Airport?
momondo data reveals that the most frequently booked airline on the route from Sarasota to Chicago Midway Airport is Southwest, representing 84% of all bookings. The subsequent popular airline is Delta at 16%.
Best airlines flying from Sarasota to Chicago Midway Airport
Compare and see reviews for airlines that fly from Sarasota to Chicago Midway Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $262 | Free Cancellation | Rating 8.0 7,963 reviews | |||
| PriceFrom $303 | Free Cancellation | Rating 8.0 4,278 reviews |
Southwest Flights From Sarasota to Chicago Midway Airport
The lowest priced Southwest flight from Sarasota to Chicago Midway Airport from the last 72 hours was $303. Generally, Southwest has 16 flights on this route every week with an average price of $379. Southwest is rated 8.0/10 by our users.
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Why should I use momondo to find a flight deal from Sarasota to Chicago?
We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Sarasota to Chicago for you.
Can I find flights from Sarasota to Chicago with flexible booking policies on momondo?
Yes. All flights to Chicago from Sarasota on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from Sarasota to Chicago?
Once all potential Sarasota to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.
I’m not ready to book a flight from Sarasota to Chicago right now. Can momondo alert me if prices change?
Price alerts on flights to Chicago from Sarasota are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.