Flights to Chicago

Compare Cheap Flights to Chicago, United States

Heading to the Windy City? Check out Webjet's latest deals, compare flights from leading airlines and find the cheapest airfare deals for your holiday to Chicago.

*Prices on this page are subject to change without notice, perform a search to view live pricing. Prices are inclusive of taxes and airline surcharges. Webjet flight fees per booking: Webjet Servicing Fee: Domestic $21.95, NZ/Pacific $24.95, International $32.95. Booking Price Guarantee: Domestic $12.95, NZ/Pacific $14.95, International $21.95. Varying payment fees are included in the price breakdown on Webjet’s checkout page, once your payment method has been selected.

Flights to Chicago Jun 2022 Jul 2022 Aug 2022 Sep 2022 Oct 2022 Nov 2022 Cheapest Flight
Departing Adelaide
$5,062 RETURN
$1,901 RETURN
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- Best Price
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Travel in October
Departing Brisbane
$4,257 RETURN
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$1,970 RETURN
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$1,970 RETURN
Travel in July
Departing Hobart - -
$2,425 RETURN
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$1,907 RETURN
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Travel in September
Departing Melbourne - - Best Price
$1,807 RETURN
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Departing Gold Coast
$8,933 RETURN
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Travel in December
Departing Perth
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$2,991 RETURN
Travel in December
Departing Sydney Best Price
$5,311 RETURN
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$5,311 RETURN
Travel in June
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Top Things to Do and See

Art Institute of Chicago

For art lovers booking return flights to Chicago, you don’t want to miss this museum. It boasts thousands of works with an impressive collection of Impressionist and post-Impressionist paintings. Some of the most famous artists at the museum include Claude Monet and Georges Seurat.


Navy Pier

The Navy Pier is one of Chicago’s top attractions. After your cheap flights to Chicago land and you’ve checked into your hotel, make your way down here for the afternoon. There are plenty of restaurants, shops, attractions and parks to explore, making it a fantastic outing for the whole family. Some of the top things to do at the Navy Pier include the Chicago’s Children’s Museum and the Crystal Gardens.


Buckingham Fountain

The Buckingham Fountain is one of the largest of its kind in the world. Every day you can see the fountain shoot 15,000 gallons of water in an impressive display. If your flights to Chicago land after sunset, you can still make your way here to watch the light show that accompanies the water.


Field Museum of Natural History

The Field Museum of Natural History is one of Chicago’s top museums. Inside the building, you’ll find a permanent collection of 20 million artefacts from all over the world including pieces from Ancient Egypt. However, the exhibit the convinces people to buy tickets to Chicago is “Sue”. It’s the largest, most complete skeleton of a Tyrannosaurus rex.


The Cost of Visiting

Hotels in Chicago

If you’re booking cheap flights to Chicago, you can save more money by staying in one of the city’s budget hotels. Rates start around $70 USD ($98 ,31 AUD) per night and go up to $150 USD ($210.67 AUD) or more if you prefer staying in apartments while abroad, you can find a room share for between $17 USD to $25 USD ($23.88 - 35.11 AUD) or an entire house for $150 USD ($210.67 AUD) per night.


Food in Chicago

It’s easy to eat cheaply in Chicago. You can expect to pay on average $20 USD ($28.09 AUD) for a meal at most of the restaurants. However, if you’re a foodie looking to buy airfare to Chicago, you’ll want to set aside some money to splurge on the fine dining options in the city. There are also plenty of farmers’ markets where you can shop for fresh produce if you prefer cooking your own meals.



The best way to get around Chicago is with the metro or public buses. You’ll pay as little as $2.25 USD ($3.16 AUD) per ride, and if you’re a student booking flights to Chicago, you can get discounts on transportation. It’s also a good idea to buy the city’s transport card so you can get unlimited rides for $10 USD ($14.04 AUD) for 24 hours and $20 USD ($28.09 AUD) for a three-day pass.


Tips for First-Time Travellers Booking Plane Tickets to Chicago

Buy the Chicago City Pass

If you’re buying flights to Chicago and you know you’re going to be visiting a lot of the city’s attractions, get the city pass. It will give you free or 50% off admission for Chicago’s top sights, and it includes a cable car and bus pass.


Use the train to get to and from O’Hare International Airport (ORD)

The best way to get from O’Hare International Airport (ORD) to your hotel is with the express train. For as little as $5, you can get from the airport to downtown Chicago in under an hour. There is also a train that connects the city to Chicago's other airport, Midway International Airport (MDW).


Download the ParkChicago App

If you’re renting a car from O’Hare International Airport (ORD), make sure you download the ParkChiciago App. Once your flights to Chicago have landed, it will help you find street parking with a few taps of your thumb. You can also use the app to pay for your parking with your credit card.


Major Events and Festivals

Taste of Chicago

The Taste of Chicago is one of the biggest outdoor festivals in the city. It’s been around since the 1980s and has grown into an event that attracts more than 3 million hungry foodies each year. If you’re booking flights to Chicago to attend the event, make sure you’ve confirmed your accommodation and airfare well in advance to lock in cheaper rates.


Chicago Jazz Festival

For music lovers booking flights to Chicago, the Chicago Jazz Festival is worth planning your trip around. It takes place over Labor Day weekend and hosts some of the world’s biggest jazz artists. It’s also Chicago’s longest running music festival.



Lollapalooza has become an institution in the United States. What started as a small music festival in 1991 has grown into one of the world’s largest live music events. If you want to attend, you’ll need to buy your tickets for the festival as soon as sales open up. It’s also a good idea to book your flights to Chicago as early as possible to avoid the price hike in airfares.

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