Cheap flights to Chicago Midway (MDW) airport from $688

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Flight deals to Chicago Midway

Looking for a cheap last-minute deal or the best return flight to Chicago Midway Airport? If you want to travel to Chicago Midway Airport next month, return fares start from $1,732. 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.

Frequently asked questions

Currently, there are no airlines that fly direct to Chicago Midway. But we found flights with one or more stops from $1,621.
The cheapest month to fly to Chicago Midway is usually August.
No airlines currently offer direct flights between Singapore and Chicago Midway Airport. Most routes have one or more stops.
The best price we found for a return flight to Chicago Midway is $1,621. 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 $990.
After crunching the numbers on our flight calendar, we found that the cheapest date to fly to Chicago Midway Airport is Thursday, 27 August 2026.
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, China Airlines offers the cheapest flight tickets to Chicago Midway.

Flying to Chicago Midway

The things to know before you go.
Cheapest flight found$688
Cheapest month to flyJuly

Discover Chicago Midway

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

  • $1,621 is currently the cheapest price for a return flight to Chicago Midway International Airport. For a one-way plane ticket to MDW, the lowest fare is $688.

  • Never pay more than you need by setting up a Price Alert for tickets to MDW. We'll keep an eye on it for you, sending updates when fares go down.

  • Pick up a bargain on tickets to Chicago, where Chicago Midway International Airport is located, by booking ahead. You're more likely to discover a great deal and have a wider range of flights to choose from.

  • Check the 'Add nearby airports' option and expand your search for cheap flights to Chicago. This will show you all the airports around your departure and arrival points.

  • If you're not in a hurry to get to Chicago, think about taking a scenic route. You might find cheaper plane tickets to Chicago Midway International Airport by choosing a flight with a stop or two.

Best time to go to Chicago

  • The cheapest month to board a flight to Chicago is usually May.

  • To find the cheapest month or even day for flights to MDW, use the 'Whole month' tool. If your travel dates are flexible, search for the green prices on the calendar — they show you the lowest available fares.

  • If you'd love to experience Chicago at its liveliest, book your flights to MDW for July. Holidaying during peak periods typically means more to see and do compared to other times.

  • Travel in November if you prefer to travel with fewer crowds. This is the quietest time of the year and also when plane tickets to Chicago are often less expensive.

  • Check the weather before travelling. July brings the warmest days in Chicago, with averages of between 16ºC (61ºF) and 28ºC (82ºF).

  • January brings the lowest temperatures, ranging from around -12ºC (10ºF) to 3ºC (37ºF).

  • Want to leave the umbrella at home? September is the driest month in Chicago, averaging six days of rain.

  • May has the wettest weather. You can expect around ten days of rainfall if you're visiting then.

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

  • Get to Chicago without any layovers. These are some of the airlines that offer direct flights to Chicago Midway International Airport:

  • If you want to jet off with the most punctual carrier, book your MDW plane ticket with Southwest Airlines. Up to 80% of its flights to this airport arrive as scheduled.

  • The local timezone at MDW is UTC-6.

  • Curl up in bed not long after your flight to MDW. Choose any of these stays near Chicago Midway International Airport and you'll be snoozing in no time:

  • Chicago Midway International Airport has an on-time performance of 76%. This number shows how often flights from MDW arrive at their destination as planned.

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

Chicago highlights

  • Put these popular attractions on your itinerary after hopping off your flight to Chicago:

    • Millennium Park: A perfect place to begin your sightseeing, this landmark is located around 0.80 kilometres northeast of the city centre in Loop.

    • Lurie Garden: You'll discover this park roughly 0.80 kilometres northeast of the centre in Loop. It's a great spot to take some time out while exploring Chicago.

    • Willis Tower: Hit up this landmark next. Around 0.48 kilometres west of the city centre in Loop, it's well worth visiting for the full Chicago experience.

How to get to Aurora from Chicago Midway International Airport (MDW)

  • The nearby city of Aurora is about 72 kilometres from MDW. The drive to the centre in a ride-share or taxi should take around 50 minutes.

  • Public transport will bring you to Aurora in 2 hours 5 minutes or so.

Travelling from Chicago Midway International Airport (MDW) to Joliet

  • About 40 kilometres away, Joliet is another city that's not far from Chicago Midway International Airport. It takes around 2 hours 10 minutes to make the journey by public transport from MDW.

  • The drive time to Joliet is roughly 45 minutes.

Explore more of the United States

  • Feel like exploring more? Indianapolis will keep things interesting on your trip through the United States. It's about 257 kilometres southeast of Chicago and features Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis. The most convenient airport for this city is Indianapolis International Airport (IND).

  • Milwaukee is another popular destination in the United States and is roughly 137 kilometres north of Chicago. Get right to the good parts at attractions like Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo. Milwaukee Mitchell International Airport (MKE) is the main gateway to this city.

  • Or head to Fort Wayne, roughly 225 kilometres east of Chicago. African-American Historical Museum, Salomon Farm Park and The Embassy Theatre are among the many reasons to visit.

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