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  1. Flights
  2. United States
  3. Chicago

Book cheap flights to Chicago from 41 $

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Discover the cheapest flights to Chicago
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Mon, 25 May - Thu, 28 May
Frontier Airlines
Frontier AirlinesDirect
Orlando - Chicago
Frontier Airlines
Frontier AirlinesDirect
Chicago - Orlando
171$
157$
Prime price per passenger
Fri, 17 Jul - Sun, 19 Jul
American Airlines
American AirlinesDirect
Newark, NJ - Chicago
American Airlines
American AirlinesDirect
Chicago - Newark, NJ
245$
225$
Prime price per passenger
Thu, 2 Jul - Sat, 4 Jul
American Airlines
American AirlinesDirect
Boston - Chicago
American Airlines
American AirlinesDirect
Chicago - Boston
244$
225$
Prime price per passenger
Thu, 18 Jun - Sun, 21 Jun
Frontier Airlines
Frontier AirlinesDirect
Atlanta - Chicago
Frontier Airlines
Frontier AirlinesDirect
Chicago - Atlanta
253$
231$
Prime price per passenger
Fri, 12 Jun - Mon, 15 Jun
Air Canada
Air CanadaDirect
Toronto - Chicago
Air Canada
Air CanadaDirect
Chicago - Toronto
258$
236$
Prime price per passenger
Fri, 24 Jul - Sun, 26 Jul
American Airlines
American AirlinesDirect
Traverse City, MI - Chicago
American Airlines
American AirlinesDirect
Chicago - Traverse City, MI
332$
306$
Prime price per passenger
Tue, 26 May
Frontier Airlines
Frontier AirlinesDirect
Los Angeles - Chicago
-15 %
48$
41$
Prime price per passenger
Tue, 16 Jun
American Airlines
American AirlinesDirect
New York City - Chicago
135$
126$
Prime price per passenger
Mon, 29 Jun
American Airlines
American AirlinesDirect
Newark, NJ - Chicago
135$
126$
Prime price per passenger
Mon, 29 Jun
American Airlines
American AirlinesDirect
Newark, NJ - Chicago
135$
126$
Prime price per passenger
Wed, 15 Jul
American Airlines
American AirlinesDirect
Newark, NJ - Chicago
135$
126$
Prime price per passenger
Thu, 23 Jul
American Airlines
American AirlinesDirect
Newark, NJ - Chicago
135$
126$
Prime price per passenger
The prices shown on this page were available within the last 20 days for the specified periods and should not be considered the final price offered. Please note that availability and prices are subject to change.

Popular flight routes to Chicago

Singapore
Flights from Singaporeto Chicago
1120$
1060$
Prime price per passenger

Book your cheap flights to Chicago

About your flight to Chicago

Chicago stands out as one of the most sought-after destinations within America. Like other destinations in United States, Chicago boasts a wealth of attractions, including a captivating culture, breathtaking architecture, and rich history, all waiting to enchant travellers.

How to find cheap tickets to Chicago

By being flexible with your travel dates and taking advantage of early booking incentives, you can maximise your savings and make the most of your Chicago experience without compromising on quality. Thus, consider also November as shoulder season for a more affordable trip with fewer tourists. Our current lowest fare is 41!

For additional savings, consider bundling a flight + hotel booking, accessing additional discounts not only for flights, but also for a variety of accommodations.

Most popular airline for Chicago

Fly to Chicago

If you're looking for a cheap plane ticket to Chicago then you've come to the right place! Edreams offers thousands of flights from the top standard and low cost airlines bringing you all the best deals on airfares to exciting destinations across the world. Simply enter your preferences in our super speedy search engine and select the best deal. It's that easy! Alternatively, whether you're an early bird or just looking for some holiday inspiration, Edreams customers can enjoy competitive prices on flights with our last minute deals to Chicago. Because we all love to save money!
Finally, and if that wasn't enough, we offer a range of other great products at low prices, including hotels and car hire, making preparing for your dream holiday with us a breeze. So what are you waiting for? Book your cheap flight to Chicago now and get away for less with Edreams.

Frequently asked questions about flights to Chicago

How can I find cheap flights to Chicago on eDreams?
At eDreams you will find flights from 41$ to Chicago. Thanks to the combination of various technologies, machine learning algorithms and real user searches on our platform, you will be able to choose between the different options that best suit your needs when you have to fly to Chicago.
When's the best time to book flights to Chicago?
By this we mean when travellers book their tickets. For the best time to actually travel to Chicago, read on.
When's the best time to go to Chicago?
According to our customers' flight searches, the best time to fly to Chicago is March.
The next best month to travel to Chicago is April.
And let's not forget February, the third top choice for travelling to Chicago.
However if you prefer things on the less busy side, we can highlight November as the least popular month for flights to Chicago.
Which airlines fly to Chicago?

Airlines flying direct from Singapore to Chicago include:

  • Frontier Airlines, with flights from Dallas, Newark, NJ and from Houston, TX, for example.
  • Spirit Airlines also operates numerous flights, some of them originating from Newark, NJ, Dallas and Fort Lauderdale.
  • American Airlines, with flights from Boston to Chicago and Newark, NJ and also from Greensboro-High Point.

Airlines with indirect flights to Chicago include:

  • Etihad Airways, which flies from Singapore, Jakarta or Vijayawada.
  • Frontier Airlines, with flights from Singapore and Bangkok, as well as from Jakarta.
  • EVA Air, with flights from Singapore, Phuket and also Ho Chi Minh City.
What is the weather like in Chicago?
If you're looking for summer vibes, the best time to travel to Chicago is in July, August and June, when the average temperature reaches 28º, while September, July and August are the 3 sunniest months of the year, with an average of 21 hours. However, if you prefer colder temperatures, make sure you visit Chicago during January, February or December to experience an average of -7º. For those who don't care too much about temperatures, but want to avoid getting wet in the rain, it's important to avoid travelling during August, July and May, when the average precipitation in Chicago is 104mm, while the months of January, February and December are drier, with an average of 49mm.

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