S$140 Cheap Flights to Chicago

View S$140 flight on Sat, 25 Oct, 2025Opens in a new window

Popular airlines to Chicago

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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.

Delta
Tue, 14 Oct - Wed, 29 Oct
LAX
Los Angeles
MDW
Chicago
S$293 Return, found 1 day ago
S$293
Return
found 1 day ago
Select Delta flight, departing Tue, 14 Oct from Los Angeles to Chicago, returning Wed, 29 Oct, priced at S$293 found 1 day ago
American Airlines
Sat, 18 Oct - Sun, 26 Oct
LAX
Los Angeles
ORD
Chicago
S$372 Return, found 6 days ago
S$372
Return
found 6 days ago
Select American Airlines flight, departing Sat, 18 Oct from Los Angeles to Chicago, returning Sun, 26 Oct, priced at S$372 found 6 days ago
United
Mon, 20 Oct - Tue, 28 Oct
LAX
Los Angeles
ORD
Chicago
S$391 Return, found 1 day ago
S$391
Return
found 1 day ago
Select United flight, departing Mon, 20 Oct from Los Angeles to Chicago, returning Tue, 28 Oct, priced at S$391 found 1 day ago
Austrian Airlines
Sun, 5 Oct - Wed, 15 Oct
LHR
London
ORD
Chicago
S$710 Return, found 2 hours ago
S$710
Return
found 2 hours ago
Select Austrian Airlines flight, departing Sun, 5 Oct from London to Chicago, returning Wed, 15 Oct, priced at S$710 found 2 hours ago
Lufthansa
Sun, 5 Oct - Wed, 15 Oct
LHR
London
ORD
Chicago
S$789 Return, found 2 hours ago
S$789
Return
found 2 hours ago
Select Lufthansa flight, departing Sun, 5 Oct from London to Chicago, returning Wed, 15 Oct, priced at S$789 found 2 hours ago

Find the cheapest month to fly from Columbus (CMH) to Chicago (CHI)

August is typically the cheapest month to fly

From S$109 - S$468 per traveller.

Frequently asked questions

What is the name of Chicago's airport?
Chicago has more than one airport, but most travellers touch down at O'Hare Intl. Airport (ORD).
How far is O'Hare Intl. Airport (ORD) from central Chicago?
The journey from O'Hare Intl. Airport (ORD) to downtown Chicago is fairly long. You'll need to travel 26 kilometres before you can check in to your city hotel.
What airport is best to fly into Chicago?
A flight to Chicago means hopping off the plane at O'Hare Airport or Chicago Airport. The first is 26 kilometres away from downtown. The second is 14 kilometres away.
How many airlines fly to Chicago?
There are a total of 51 airlines connecting Chicago with 237 airports globally.
Which airlines fly to Chicago?
Chicago receives the highest number of flights from United Airlines, American Airlines and Delta with United Airlines being the number one choice of airline. New York is the most popular city for passengers to jet off from.
How many nonstop flights are there to Chicago?
With roughly 7,564 nonstop flights running every week, you'll be hitting the runway in Chicago before you can ask, "Are we there yet?"
Where are the most popular flights to Chicago departing from?
The most popular flights to Chicago set off from New York, Washington and Dallas airports.
How long is the flight to Chicago Airport?
If it's New York you're leaving behind, you'll be in the air for around 2 hours and 44 minutes before you arrive in Chicago. Terminal to terminal from Washington generally takes 2 hours and 15 minutes and from Dallas, the average flight time is 2 hours and 18 minutes.
How to book the cheapest flight to Chicago?
Don't leave booking your flight to Chicago until the last minute. That's one trick seasoned travellers use to get the best prices. Booking well in advance means more choices and cheaper flights. Don't stop there, however. Do some research and see if there is more than one airport at your destination. Fares often differ depending on which airport you go for. Don't forget to compare fares across air carriers too. Finally, another easy way to save a few dollars is be ready to book at a moment's notice. If you stumble on a good bargain, don't hold off — grab it while you can.
Do you have any tips for my flight to Chicago?
Depending on where you're coming from, your trip to Chicago could be simple and straightforward or it could go on forever. We've put together some handy tips that will help you start your next unforgettable escape on the right foot. What to pack in your hand luggage:

  • It's simple — first, pack your passport, travel documents, wallet and daily medications. Next, you'll need some in-flight entertainment to while away the hours. A thrilling book and a laptop filled with your favourite shows are some wonderful options. If you intend to take a quick nap, a neck pillow and a pair of earplugs will also be useful. Finally, leave some space for a few toiletry items to ensure you touchdown feeling fresh and raring to go.

Do not pack the following items in your hand luggage:

  • Leave all your full-sized bottles of shampoo and hair gel in your checked luggage. Any gels or liquids in your carry-on suitcase larger than 3.4 ounces (100 millilitres) will be confiscated. Sharp or pointed objects, like a Swiss Army knife, and dangerous products which are explosive or flammable, such as spray paint, flares and fireworks, are also restricted.

What to wear on a flight:

  • Choose comfort over style. Prepare for changes in temperature by donning layers, and opt for flat, enclosed shoes like sneakers.
  • Most of us have heard about deep vein thrombosis (DVT), a blood clot condition caused by long periods of inactivity. To reduce your risk on board, stay hydrated, consider wearing compression socks and move your lower limbs often.

How to get through airport security fast when flying to Chicago?
The secret is to be well prepared before you arrive at airport security. That way, you'll be boarding that plane to Chicago in a flash. Follow these helpful tips and get your holiday off to a fantastic start:

  • First things first. Your passport and boarding pass will need to be shown to airport security personnel. Keep them at hand so you don't have to dig around for them.
  • Your belt, jacket, keys and other small items, like your headphones, will need to go through the X-ray machine. Make the whole process faster by removing them as your turn draws near.
  • For just a few moments, you'll need to unplug from the digital world. Your phone, laptop and any other electronic gadgets will need to go through the scanner.
  • Remove all gels and liquids from your hand luggage. They often need to be sent through the X-ray machine separately. Each product should be in a container no larger than 3.4 ounces (100 millilitres) and everything must fit inside a single quart-size (one litre), clear zip-close bag.
  • The right choice of footwear can save you several minutes. Boots are often required to be removed and X-rayed separately. Slip-on shoes usually aren't.
  • Airlines will not allow any sharp objects to come on board with you. If you must bring these kinds of items, check them in.

Book with confidence

Book with confidence

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.

Cheap flights to Chicago

Travel information

Travel information

Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Return price
S$202

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.

All Nippon Airways
Mon, 20 Oct - Tue, 4 Nov
SIN
Singapore
ORD
Chicago
S$1,083 Return, found 7 hours ago
S$1,083
Return
found 7 hours ago
Select All Nippon Airways flight, departing Mon, 20 Oct from Singapore to Chicago, returning Tue, 4 Nov, priced at S$1,083 found 7 hours ago

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