186 € Cheap Flights from Sarasota to Chicago Midway

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      Travellers and cabin class, 1 Adult, Economy
      Southwest Airlines

      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 return flight from Sarasota Airport to Chicago Midway Airport? If you want to travel next month, return fares start from 203 €. Find the lowest prices on one-way and return 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 October.

      Direct flights from Sarasota to Chicago Midway

      Southwest Airlines

      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 found186 €
      Cheapest month to flyOctober
      Average flight time2 hrs, 49 mins
      Most popular airlineSouthwest Airlines
      Average flights per week13

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

      The best price we found for a return flight from Sarasota to Chicago Midway is 186 €. 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 49 minutes is the average flight time from Sarasota to Chicago Midway.
      Southwest Airlines flies direct from Sarasota to Chicago Midway.
      As of August 2026, there are 13 flights per week flying from Sarasota to Chicago Midway.
      The cheapest month to fly from Sarasota to Chicago Midway is usually October.
      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 Thursday, 15 October 2026.
      Yes – the average flight time is 2 hours and 49 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.

      Flying from Sarasota Airport (SRQ) to Chicago Midway Airport (MDW): what you need to know

      • The average duration of a direct flight from Sarasota Airport to Chicago Midway Airport is 2 hours 45 minutes.

      • Chicago is one hour behind Sarasota and follows the UTC-6 timezone.

      • You can choose from six weekly Sarasota Airport to Chicago Midway Airport flights. The 06:00 departure with Southwest Airlines is the earliest flight available. Southwest Airlines operates the latest service of the day at 20:00.

      • Arriving two hours before an international flight and one hour ahead of a domestic departure are golden rules for stress-free travel. Be at the airport with enough time to board your SRQ to MDW flight.

      • You'll likely experience longer queues in popular months such as April. Arriving up to four hours ahead of international flights and two hours for a domestic departure is a wise move.

      • Southwest Airlines has direct flights from Sarasota Airport to Chicago Midway Airport. Book with this popular carrier, then get ready to see the sights in Chicago — and maybe even more of the United States if you have time.

      • Most passengers choose to travel with Southwest Airlines on this route.

      • With 76.34% of services arriving as scheduled, Southwest Airlines is the most punctual carrier operating SRQ to MDW flights.

      • If you'd like to split up your journey, simply uncheck 'Direct flights only' when searching for your ticket from Sarasota Airport to Chicago Midway Airport. Here are the top stopovers between SRQ and MDW:

        • Atlanta Hartsfield-Jackson Airport

        • Detroit Wayne County Airport

        • Nashville Airport

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

      • Currently, 93 € is the lowest price we've seen for a one-way Sarasota Airport to Chicago Midway Airport flight. The best price for a return ticket is 186 €. Keep in mind that fares may change due to availability at the time of booking.

      • To get your hands on cheap tickets from SRQ to MDW, book as early as you can. Airlines typically offer the most competitive fares when flights are first made available.

      • Organise your trip for May. That's the cheapest month for flights from Sarasota Airport to Chicago Midway Airport. If you're flexible with your travel dates, use the 'Whole month' tool to see the cheapest price across each month.

      • You don't need to check back in every day to see if fares have dropped when you create a Price Alert. We'll let you know as soon as there's a better deal on cheap flights from SRQ to MDW.

      • Lock in the perfect flight for you with the help of the filters. To see the 'Best,' 'Cheapest' or 'Fastest' flights from Sarasota Airport to Chicago Midway Airport, use the 'Sort by' tool. You can also filter by airline, arrival and departure times, and number of stops.

      Handy information about Sarasota Airport (SRQ)

      • You'll find SRQ at 6000 Airport Circle.

      • Sarasota Airport has an excellent on-time record, so you're less likely to experience disruptions. Departures from SRQ land on schedule 80% of the time.

      • To reach Sarasota Airport from central Sarasota, it'll take about 15 minutes if you're travelling by car. This depends on traffic though. It's approximately 11 kilometres from the airport to the city centre.

      • You can expect a journey time of around 35 minutes when using public transport.

      • Searching for a handy hotel near SRQ? If you're boarding an early flight from Sarasota Airport to Chicago Midway Airport, these stays will have you sleeping moments from your departure lounge:

      Arriving at Chicago Midway Airport (MDW)

      • Consider staying in a hotel close to MDW if you're on a late Sarasota Airport to Chicago Midway Airport flight. Select one of these accommodation options and skip the long transfer:

      • Pick up a Chicago Midway Airport rental car and discover Chicago and beyond with your own wheels. Dollar, Hertz and Budget are leading providers you can book with here.

      • Reserving your vehicle from Chicago Midway Airport around four weeks in advance boosts your odds of scoring a great price.

      When to fly to Chicago Midway Airport (MDW)

      • The quietest month for a flight from Sarasota Airport to Chicago Midway Airport is December, while July is the most popular. Pick the best time to visit Chicago based on whether you prefer a laid-back vibe or a more bustling atmosphere.

      • Lock in your flight from Sarasota Airport to Chicago Midway Airport for July if you want to explore Chicago during its warmest month. You can expect temperatures of between 16ºC (61ºF) and 28ºC (82ºF).

      • If you'd rather travel in cooler conditions, look for a cheap ticket from SRQ to MDW in January. Average temperatures are between -12ºC (10ºF) and 3ºC (37ºF) then.

      Explore more of the United States

      • Columbus is just one of the many cities in the United States waiting to be explored after you've experienced Chicago. Around 451 kilometres away to the south-east, its top attractions include Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

      • Indianapolis is another standout destination in the United States and is around 257 kilometres south-east of Chicago. No journey is complete without experiencing Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

      Prices shown on this page are estimated lowest prices only. Found in the last 12 days.