Cheap Flights from Sarasota (SRQ) to Chicago Midway (MDW)

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      Compare Sarasota to Chicago Midway flight deals

      Find the cheapest month or even day of the year to fly to Chicago Midway

      Book the best Chicago Midway fare with no extra fees

      Flight deals from Sarasota to Chicago Midway

      Looking for a cheap last-minute deal or the best round-trip flight from Sarasota to Chicago Midway? Find the lowest prices on one-way and round-trip tickets right here.

      Find the cheapest month to fly from Sarasota to Chicago Midway

      We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Sarasota to Chicago Midway flights are currently cheapest in June.

      Direct flights from Sarasota to Chicago Midway

      Sarasota to Chicago Midway: Alternative routes

      Compare routes from Sarasota to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

      Sarasota to Chicago: Flight information

      The things to know before you go.
      Cheapest flight found$88
      Cheapest month to flyJune
      Average flight time2 hrs, 46 mins
      Most popular airlineSouthwest Airlines
      Average flights per week9

      Finding cheap flights from Sarasota to Chicago Midway: Frequently asked questions

      The best price we found for a round-trip flight from Sarasota to Chicago Midway is $301. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
      2 hours and 46 minutes is the average flight time from Sarasota to Chicago Midway.
      Southwest Airlines flies direct from Sarasota to Chicago Midway.
      There are 9 flights per week flying from Sarasota to Chicago Midway, as of May 2025.
      The cheapest month to fly from Sarasota to Chicago Midway is usually July.
      After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Sarasota Airport to Chicago Midway Airport on Wednesday, July 9, 2025.
      Yes – the average flight time is 2 hours and 46 minutes.
      We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
      We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
      Currently, Southwest Airlines offers the cheapest flight tickets to Chicago Midway.

      Traveling from Sarasota Bradenton International Airport (SRQ) to Chicago Midway International Airport (MDW): what you need to know

      • The average time for a direct flight from Sarasota Bradenton International Airport to Chicago Midway International Airport is 2 hours 45 minutes.

      • Chicago is one hour behind Sarasota and is in the UTC-5 timezone.

      • Flights from SRQ to MDW start from 05:45 — the earliest with Southwest Airlines. The last departure is at 20:00 with Southwest Airlines. In total, there are six weekly Sarasota Bradenton International Airport to Chicago Midway International Airport flights.

      • Leave enough time to catch your SRQ to MDW flight. As a rule of thumb, arrive two hours before international departures and an hour ahead for domestic flights.

      • During popular months such as July, it's a good idea to get to the airport even earlier. Arrive two hours before domestic departures and four hours ahead for international flights whenever you're traveling during peak periods in general.

      • Southwest Airlines is your ticket to exploring Chicago (and maybe even some other great corners of United States!). Browse the direct flights from Sarasota Bradenton International Airport to Chicago Midway International Airport offered by this popular carrier.

      • The majority of passengers choose to fly with Southwest Airlines on this route.

      • With 76.12% of its services landing on schedule, Southwest Airlines is the most punctual carrier offering SRQ to MDW flights.

      • If you want to break up your flight, simply uncheck 'Direct flights only' when searching for your ticket from Sarasota Bradenton International Airport to Chicago Midway International Airport. These are the most popular stopovers between SRQ and MDW:

        • Nashville International Airport

        • Hartsfield-Jackson Atlanta International Airport

        • Detroit Metropolitan Wayne County Airport

      How to find the cheapest flights from Sarasota Bradenton International Airport (SRQ) to Chicago Midway International Airport (MDW)

      • The lowest price we've found for a one-way Sarasota Bradenton International Airport to Chicago Midway International Airport flight is $88. A return plane ticket right now is $301. Depending on the availability and when you book, these fares may change.

      • Book six months before you want to fly. After looking at the numbers on our calendar, this is how far you'll want to book ahead to secure cheap tickets from SRQ to MDW.

      • May is the cheapest month for flights from Sarasota Bradenton International Airport to Chicago Midway International Airport. If you'd like to fly at a different time of year, the 'Whole month' tool will give you the lowest prices across every month.

      • You don't need to check back in every day to see if fares have dropped when you set up a Price Alert. We'll send you an update the moment a special offer becomes available on cheap flights from SRQ to MDW.

      • Select your ideal departure and arrival times, number of stops and airlines with the filters. Or sort your results by 'Cheapest' to see the best deals on flights from Sarasota Bradenton International Airport to Chicago Midway International Airport.

      Handy information about Sarasota Bradenton International Airport (SRQ)

      • SRQ is located at 6000 Airport Circle.

      • 78.61% of flights that take off from Sarasota Bradenton International Airport reach their destination on time.

      • Central Sarasota to Sarasota Bradenton International Airport is approximately 5 miles. Depending on traffic, it'll take about 10 minutes to get there if you're driving, ride-sharing or catching a cab.

      • The trip when using public transport usually takes 1 hour 5 minutes.

      • Searching for a handy hotel close to SRQ? If you're boarding an early flight from Sarasota Bradenton International Airport to Chicago Midway International Airport, these accommodation options will have you sleeping moments from check-in:

      Arriving at Chicago Midway International Airport (MDW)

      Getting from Chicago Midway International Airport (MDW) to central Chicago

      • MDW is located at 5700 South Cicero.

      • From Chicago Midway International Airport, Chicago is approximately 12 miles away. It takes around 20 minutes to drive to the center.

      • It takes around 45 minutes to get there by public transport.

      When to fly to Chicago Midway International Airport (MDW)

      • It's time to plan your travel dates for your flight from Sarasota Bradenton International Airport to Chicago Midway International Airport. July is the most popular month to visit Chicago. If you want a more laid-back vibe, go in May.

      • Before locking in your flight from Sarasota Bradenton International Airport to Chicago Midway International Airport, consider the type of weather you like. July is the warmest month in Chicago, with the temperature ranging from 59ºF to 84ºF.

      • If you like cooler conditions, look for a cheap ticket from SRQ to MDW in January. Temperatures average between 10ºF and 37ºF then.

      Explore more of United States

      • Chicago has its own special appeal, but there are so many other corners of United States waiting to be discovered. About 280 miles south-east of Chicago, a trip to Columbus will keep you on the go. Don't miss top attractions like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

      • Indianapolis is another favorite destination in United States and is around 160 miles south-east of Chicago. No trip is complete without visiting The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

      Prices shown on this page are estimated lowest prices only. Found in the last 45 days.