Cheap Flights to Chicago Midway Airport (MDW)

Travellers and cabin class

Compare Chicago Midway Airport flights across hundreds of providers

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

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Flight deals to Chicago Midway

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

Find the cheapest time to fly to Chicago Midway

Flexible on travel dates? Find the cheapest month – or even day – to fly to Chicago Midway.

Airports near Chicago

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

Frequently asked questions

Currently, there are no airlines that fly direct to Chicago Midway. But we found flights with one or more stops from 462 €.
The cheapest month to fly to Chicago Midway is usually October.
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.
No airlines currently offer direct flights between Ireland and United States. Most routes have one or more stops.
The best price we found for a return flight to Chicago Midway is 462 €. 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.
We found flights to Chicago O'Hare International Airport, which is 25.4 km from Chicago, from 308 €.
After crunching the numbers on our flight calendar, we found that the cheapest date to fly to Chicago Midway Airport is Thursday, 30 October 2025.
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, Delta offers the cheapest flight tickets to Chicago Midway.

Flying to Chicago Midway

The things to know before you go.
Cheapest flight found462 €
Cheapest month to flyOctober

How to find cheap flights to Chicago Midway International Airport (MDW)

  • 462 € is currently the cheapest price we've seen for a return flight to Chicago Midway International Airport. For a one-way plane ticket to MDW, the lowest fare is 299 €.

  • Book at the perfect time with Price Alerts. You'll get an email or a notification on the app if the price of tickets to MDW changes.

  • It's generally recommended to book roughly six months before your departure date. That's when you're likely to get the best price on tickets to Chicago, where Chicago Midway International Airport is located.

  • Click on the 'Add nearby airports' filter and expand your search for cheap flights to Chicago. This will list every airport around your departure and arrival points.

  • If you aren't in a rush to get to Chicago, consider taking a little detour. You could find cheaper plane tickets to Chicago Midway International Airport by choosing a flight with one or more stops.

Best time to go to Chicago

  • May is generally the cheapest month to hop on a flight to Chicago.

  • If you can be flexible with your dates, try using the 'Whole month' tool. It'll show you the cheapest month, and even day of the year, for flights to MDW.

  • If you'd like to experience Chicago at its liveliest, book your flights to MDW for July. Being on holiday during high seasons typically means more things to do compared to other times.

  • Travel in May if you'd rather avoid the crowds. This is the quietest period of the year and also when plane tickets to Chicago are often more affordable.

  • The weather can make or break a holiday, so consider the type of conditions you enjoy travelling in. Chicago is warmest in July, with averages of between 15ºC and 29ºC.

  • January has the lowest temperatures, ranging from about -12ºC to 3ºC.

Travelling to Chicago Midway International Airport (MDW): what you need to know

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

Chicago highlights

Millennium Park

  • Around 0.80 kilometres north-east of the centre in Loop, Millennium Park should be on your travel itinerary. Make it one of your first stops after your flight to Chicago Midway International Airport.

Art Institute of Chicago

  • Drop by Art Institute of Chicago and you'll be crossing off one of the top attractions in Chicago. It's roughly 0.48 kilometres east of the centre in Loop.

LandShark Beer Garden at Navy Pier

  • From the heart of the city, this highlight is around 2 kilometres north-east. It's located in the Loop area and a classic addition to any Chicago visit.

Complete your trip with a Chicago car hire

  • Explore our car rentals in Chicago once you've reserved your hotel and cheap flight to Chicago Midway International Airport. All the best offers are in one place, making it simple to compare prices and take off in your dream ride.

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