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Cheap flights from Chicago Midway Airport

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Fast facts on flights from Chicago Midway

Cheapest flight foundMiami, $54
Cheapest month to flyMay
Most popular destinationSingapore
Most popular airlineSouthwest Airlines

The best flight deals leaving from Chicago Midway Airport soon

Save on your flight fare, so you can spend more when you get there. Here are the best domestic and international flights from Chicago Midway Airport departing soon.
Dallas.$54 per passenger.Departing Tue, 7 May, returning Tue, 14 May.Return flight with Frontier Airlines.Outbound direct flight with Frontier Airlines departs from Chicago Midway on Tue, 7 May, arriving in Dallas Fort Worth International.Inbound direct flight with Frontier Airlines departs from Dallas Fort Worth International on Tue, 14 May, arriving in Chicago Midway.Price includes taxes and charges.From $54, select.
Toronto.$337 per passenger.Departing Thu, 13 Jun, returning Sat, 15 Jun.Return flight with Porter Airlines (Canada) Ltd.Outbound direct flight with Porter Airlines (Canada) Ltd departs from Chicago Midway on Thu, 13 Jun, arriving in Toronto Island.Inbound direct flight with Porter Airlines (Canada) Ltd departs from Toronto Island on Sat, 15 Jun, arriving in Chicago Midway.Price includes taxes and charges.From $337, select.
San Juan.$379 per passenger.Departing Sun, 5 May, returning Sat, 11 May.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sun, 5 May, arriving in San Juan Luis Munoz Marin.Inbound indirect flight with Frontier Airlines, departs from San Juan Luis Munoz Marin on Sat, 11 May, arriving in Chicago Midway.Price includes taxes and charges.From $379, select.
Tulum.$391 per passenger.Departing Sun, 2 Jun, returning Wed, 12 Jun.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Sun, 2 Jun, arriving in Tulum Felipe Carrillo.Inbound indirect flight with Delta, departs from Tulum Felipe Carrillo on Wed, 12 Jun, arriving in Chicago Midway.Price includes taxes and charges.From $391, select.
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Booking flights from Chicago Midway Airport: frequently asked questions

The best price we found for a return flight from Chicago Midway to Dallas is $54. 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.
After crunching the numbers on our flight calendar, we found that the cheapest date to fly out of Chicago Midway Airport is Tuesday, 7 May 2024, to Dallas Fort Worth International Airport.
It's easy with us. Look for cheap flights and flight offers from Chicago Midway Airport to anywhere using Everywhere search – it'll show you the lowest fares for your chosen time period.

You can also set up Price Alerts for flights you'd like to keep an eye on. We'll let you know when a particular fare from Chicago Midway Airport rises or falls so you can book when it's cheapest.
Sure – our flight search allows you to check for outbound flights from Chicago Midway departing the very same day. But if you want the cheapest fare, we recommend you book around 30 days before departure. This is on average, the time when fares are cheaper.
Of course! Just select 'one way' when you search with us. And here's an extra tip: sometimes searching for a one way ticket from Chicago Midway Airport, and another one-way back home, can yield cheaper tickets than a return fare with an airline.
It's best to arrive at Chicago Midway Airport at least 2 hours before the time of your flight departure, so you have enough time to check any luggage in, clear security and find your gate.
The cheapest flight from Chicago Midway Airport we found in the next 1 year is to Dallas Fort Worth International for $54. It departs on Tuesday, 7 May 2024. There are also cheap flights from Chicago Midway Airport to Toronto Island and San Juan Luis Munoz Marin.

How to find cheap flights from Chicago Midway

Looking for cheap tickets from Chicago Midway? Whether you are flying one-way or return, here are a few tips on how to score the best price and make your flight journey as smooth as possible.

  • Enter your destination and hit 'search'. We've compared flights from all major airlines and online travel agents to find the cheapest flight tickets from Chicago Midway. And with us there are no hidden fees - what you see is what you pay.
  • Search flights everywhere. Not sure on the destination just yet? You can easily browse available places to travel to from Chicago Midway by searching flights to 'Everywhere'.
  • Flex your dates to secure the best fares for your flight from Chicago Midway. If your travel dates are flexible, use Skyscanner's 'Whole month' tool to find the cheapest month, and even day to fly from Chicago Midway.
  • Set up a Price Alert. We price check with over 1000 travel companies so you don't have to. You can easily track the price of your tickets from Chicago Midway by creating an alert. Whenever prices go down or up, you'll get an email or push notification to help make sure you get the best possible flight deal.
  • Look for direct flights. Only interested in non-stop flights from Chicago Midway? Make sure to tick 'Direct flights' when performing a search. If there are direct flights from Chicago Midway available, these will appear in the results.
  • Find the cheapest Business Class flights from Chicago Midway. Check the difference in price of your plane ticket from Chicago Midway when travelling in Economy, Premium Economy, Business or First Class. Note that not all cabin classes are available for every destination or airline.
  • Include nearby airports in your search. Widen your search for flight deals from Chicago Midway by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure and destination point and could help you save money.
  • Search for flight tickets on the go. To get the best flight booking experience on the go, download our app and search for cheap flight tickets from Chicago Midway when out and about.

Book a flight from Chicago Midway with extra peace of mind

  • Find flexible flights from Chicago Midway. Your airline might be offering flexible tickets from Chicago Midway, which means you won't lose out if your flight has to be changed or cancelled.
  • Add travel cost protection. Make sure you have the right travel insurance before flying from Chicago Midway. That way you can cover the costs of any unexpected events, such as delays or lost luggage.

Combine your flight from Chicago Midway with hotels and car hire

Once you've secured your plane ticket from Chicago Midway we will also help you discover the best prices and exclusive rates for hotels in or close to your destination. Compare hundreds of car hire companies in one go so that you get the best car hire deals for your trip.