S$379 Cheap Flights to Chicago

Cheap round-trip flights to Chicago

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

Turkish Airlines
Turkish Airlines
All Nippon Airways

Reviews from verified customers

17 Apr 2019

There was one broken luggage when I picked up ,there was a big crack on the wheel.

A verified traveller
Toronto to Chicago · All Nippon Airways
30 Mar 2019

Flight was delayed. We hope that it was on time

A verified traveller
New York to Chicago · Delta

Cheap flights to Chicago

One of the most iconic cities in the USA, Chicago is home to towering skyscrapers, legendary sports teams, great food and a vibrant cultural scene. Book flights to Chicago and you can explore everything the Windy City has to offer.

When to book flights to Chicago

Summer is the busiest time for tourists visiting Chicago. The weather is warm, the skies are generally clear and the city hosts numerous festivals throughout June, July and August. Although the popularity of the summer months can make it more of a challenge to find cheap flights to Chicago, if you know where to look finding a great deal should still be possible.

If you want to avoid the crowds of the summer months, visit Chicago in April, May, September or October. Attractions, sports events and hotels are normally quieter during the autumn and spring months, making it easy for you to make the most of the city during your stay.

Winters in Chicago can be bitingly cold, with the city’s famous winds making the temperature feel even lower. Unless all of the attractions you’re planning to see are indoor, it might be best to plan your trip outside of the winter season.

How to find cheap flights to Chicago

Whenever you decide to plan your trip to Chicago, using Expedia will help you to find the best value deals available.

Alternatively, you can click the ‘Nearby Airports’ option once your flights are returned to see if there are any other nearby airports with cheap Chicago flights.

You can narrow down your flight options by airline, departure time and travel time using the filters on the left-hand side of the results page.

Main Airports in Chicago

Chicago is home to two large international airports.

Chicago O’Hare and Chicago Midway. O’Hare International is one of the world’s busiest airports and sees millions of people pass through its terminals every year. Located around 27 miles northwest of central Chicago, it’s connected to the city via the ‘L’ train as well as buses, taxis and airport shuttles.

The city’s second airport is Chicago Midway. Located just eight miles from The Loop (Chicago’s central district), it serves a wide choice of domestic airports as well as a few selected international destinations. Like O’Hare, Chicago Midway is on the city’s public transport network.

Which airlines fly to Chicago?

These include:

  • Finnair
  • Iberia
  • British Airways
  • American Airlines
  • Austrian Airlines
  • United
  • Brussels Airlines
  • Lufthansa
  • Aer Lingus
  • Icelandair

How to get around Chicago

Chicago’s public transport network is the second most extensive in the United States.

The fastest and most convenient form of public transport in the city is the ‘L’ train. An icon of Chicago, it connects the entire central area of the city as well as some outlying neighbourhoods.

Buses also run on routes all over the city, making it easy to reach your destination no matter where you’re off to.

The centre of Chicago is easy to navigate on foot. A number of attractions are within walking distance of each other. Alternatively, you can hire a bike and explore Chicago on two wheels.

Must-see attractions in Chicago

When you touch down in the Windy City, the first sightseeing spot on your itinerary should be Millennium Park. This 25-acre site is known for its free concerts and events and makes a great destination for an afternoon stroll or a bit of people watching.

Another must see sight in Chicago is Navy Pier. Originally opened in 1916, the pier is home to a great choice of attractions, shops, eateries and gardens.

Frequently asked questions

Trending flights to Chicago

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

Turkish Airlines
Turkish Airlines