Chicago (CHI) Flights

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Cheap Chicago Flights

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sun., 19 Jan. - Sun., 26 Jan.
SYD
Kingsford Smith Intl.
ORD
O'Hare Intl.
AU$1,333 Return, found 3 days ago
AU$1,333
Return
found 3 days ago
Select American Airlines flight, departing Sun., 19 Jan. from Kingsford Smith Intl. to O'Hare Intl., returning Sun., 26 Jan., priced at AU$1,333 found 3 days ago
American Airlines
Sun., 19 Jan. - Sun., 26 Jan.
SYD
Kingsford Smith Intl.
ORD
O'Hare Intl.
AU$1,344 Return, found 3 days ago
AU$1,344
Return
found 3 days ago
Select American Airlines flight, departing Sun., 19 Jan. from Kingsford Smith Intl. to O'Hare Intl., returning Sun., 26 Jan., priced at AU$1,344 found 3 days ago
Qantas Airways
Sun., 19 Jan. - Sun., 26 Jan.
SYD
Kingsford Smith Intl.
ORD
O'Hare Intl.
AU$1,515 Return, found 3 days ago
AU$1,515
Return
found 3 days ago
Select Qantas Airways flight, departing Sun., 19 Jan. from Kingsford Smith Intl. to O'Hare Intl., returning Sun., 26 Jan., priced at AU$1,515 found 3 days ago
Qantas Airways
Sun., 19 Jan. - Sun., 26 Jan.
SYD
Kingsford Smith Intl.
ORD
O'Hare Intl.
AU$1,515 Return, found 3 days ago
AU$1,515
Return
found 3 days ago
Select Qantas Airways flight, departing Sun., 19 Jan. from Kingsford Smith Intl. to O'Hare Intl., returning Sun., 26 Jan., priced at AU$1,515 found 3 days ago
Qantas Airways
Sun., 19 Jan. - Sun., 26 Jan.
SYD
Kingsford Smith Intl.
ORD
O'Hare Intl.
AU$1,585 Return, found 3 days ago
AU$1,585
Return
found 3 days ago
Select Qantas Airways flight, departing Sun., 19 Jan. from Kingsford Smith Intl. to O'Hare Intl., returning Sun., 26 Jan., priced at AU$1,585 found 3 days ago
American Airlines
Sun., 19 Jan. - Sun., 26 Jan.
SYD
Kingsford Smith Intl.
ORD
O'Hare Intl.
AU$1,998 Return, found 3 days ago
AU$1,998
Return
found 3 days ago
Select American Airlines flight, departing Sun., 19 Jan. from Kingsford Smith Intl. to O'Hare Intl., returning Sun., 26 Jan., priced at AU$1,998 found 3 days ago
Qantas Airways
Sun., 19 Jan. - Sun., 26 Jan.
SYD
Kingsford Smith Intl.
ORD
O'Hare Intl.
AU$1,998 Return, found 3 days ago
AU$1,998
Return
found 3 days ago
Select Qantas Airways flight, departing Sun., 19 Jan. from Kingsford Smith Intl. to O'Hare Intl., returning Sun., 26 Jan., priced at AU$1,998 found 3 days ago
Qantas Airways
Sun., 19 Jan. - Sun., 26 Jan.
SYD
Kingsford Smith Intl.
ORD
O'Hare Intl.
AU$2,000 Return, found 3 days ago
AU$2,000
Return
found 3 days ago
Select Qantas Airways flight, departing Sun., 19 Jan. from Kingsford Smith Intl. to O'Hare Intl., returning Sun., 26 Jan., priced at AU$2,000 found 3 days ago
American Airlines
Sun., 19 Jan. - Sun., 26 Jan.
SYD
Kingsford Smith Intl.
ORD
O'Hare Intl.
AU$2,008 Return, found 3 days ago
AU$2,008
Return
found 3 days ago
Select American Airlines flight, departing Sun., 19 Jan. from Kingsford Smith Intl. to O'Hare Intl., returning Sun., 26 Jan., priced at AU$2,008 found 3 days ago
Qantas Airways
Sun., 19 Jan. - Sun., 26 Jan.
SYD
Kingsford Smith Intl.
ORD
O'Hare Intl.
AU$2,053 Return, found 3 days ago
AU$2,053
Return
found 3 days ago
Select Qantas Airways flight, departing Sun., 19 Jan. from Kingsford Smith Intl. to O'Hare Intl., returning Sun., 26 Jan., priced at AU$2,053 found 3 days ago
Qantas Airways
Sun., 19 Jan. - Sun., 26 Jan.
SYD
Kingsford Smith Intl.
ORD
O'Hare Intl.
AU$2,053 Return, found 3 days ago
AU$2,053
Return
found 3 days ago
Select Qantas Airways flight, departing Sun., 19 Jan. from Kingsford Smith Intl. to O'Hare Intl., returning Sun., 26 Jan., priced at AU$2,053 found 3 days ago
American Airlines
Sun., 19 Jan. - Sun., 26 Jan.
SYD
Kingsford Smith Intl.
ORD
O'Hare Intl.
AU$2,061 Return, found 3 days ago
AU$2,061
Return
found 3 days ago
Select American Airlines flight, departing Sun., 19 Jan. from Kingsford Smith Intl. to O'Hare Intl., returning Sun., 26 Jan., priced at AU$2,061 found 3 days ago
Qantas Airways
Sun., 19 Jan. - Sun., 26 Jan.
SYD
Kingsford Smith Intl.
ORD
O'Hare Intl.
AU$2,069 Return, found 3 days ago
AU$2,069
Return
found 3 days ago
Select Qantas Airways flight, departing Sun., 19 Jan. from Kingsford Smith Intl. to O'Hare Intl., returning Sun., 26 Jan., priced at AU$2,069 found 3 days ago
American Airlines
Sun., 19 Jan. - Sun., 26 Jan.
SYD
Kingsford Smith Intl.
ORD
O'Hare Intl.
AU$2,072 Return, found 3 days ago
AU$2,072
Return
found 3 days ago
Select American Airlines flight, departing Sun., 19 Jan. from Kingsford Smith Intl. to O'Hare Intl., returning Sun., 26 Jan., priced at AU$2,072 found 3 days ago
American Airlines
Sun., 19 Jan. - Sun., 26 Jan.
SYD
Kingsford Smith Intl.
ORD
O'Hare Intl.
AU$2,079 Return, found 3 days ago
AU$2,079
Return
found 3 days ago
Select American Airlines flight, departing Sun., 19 Jan. from Kingsford Smith Intl. to O'Hare Intl., returning Sun., 26 Jan., priced at AU$2,079 found 3 days ago
American Airlines
Sun., 19 Jan. - Sun., 26 Jan.
SYD
Kingsford Smith Intl.
ORD
O'Hare Intl.
AU$2,088 Return, found 3 days ago
AU$2,088
Return
found 3 days ago
Select American Airlines flight, departing Sun., 19 Jan. from Kingsford Smith Intl. to O'Hare Intl., returning Sun., 26 Jan., priced at AU$2,088 found 3 days ago
American Airlines
Sun., 19 Jan. - Sun., 26 Jan.
SYD
Kingsford Smith Intl.
ORD
O'Hare Intl.
AU$2,099 Return, found 3 days ago
AU$2,099
Return
found 3 days ago
Select American Airlines flight, departing Sun., 19 Jan. from Kingsford Smith Intl. to O'Hare Intl., returning Sun., 26 Jan., priced at AU$2,099 found 3 days ago
All Nippon Airways
Sun., 24 Nov. - Tue., 10 Dec.
SYD
Kingsford Smith Intl.
ORD
O'Hare Intl.
AU$2,118 Return, found 1 day ago
AU$2,118
Return
found 1 day ago
Select All Nippon Airways flight, departing Sun., 24 Nov. from Kingsford Smith Intl. to O'Hare Intl., returning Tue., 10 Dec., priced at AU$2,118 found 1 day ago
All Nippon Airways
Sun., 24 Nov. - Mon., 2 Dec.
SYD
Kingsford Smith Intl.
ORD
O'Hare Intl.
AU$2,121 Return, found 2 days ago
AU$2,121
Return
found 2 days ago
Select All Nippon Airways flight, departing Sun., 24 Nov. from Kingsford Smith Intl. to O'Hare Intl., returning Mon., 2 Dec., priced at AU$2,121 found 2 days ago
Qantas Airways
Sun., 19 Jan. - Sun., 26 Jan.
SYD
Kingsford Smith Intl.
ORD
O'Hare Intl.
AU$2,123 Return, found 3 days ago
AU$2,123
Return
found 3 days ago
Select Qantas Airways flight, departing Sun., 19 Jan. from Kingsford Smith Intl. to O'Hare Intl., returning Sun., 26 Jan., priced at AU$2,123 found 3 days ago

Deals On This Weekend's Flights

Chicago Flight Info

Destination Airport
Destination
Airlines Serving
Flights Prices Starting At
AU$1,333

Chicago Flights

Everyone from Kanye Westto Frank Sinatra has fallen for this town, and while one might serenade it in a slightly classier fashion, there’s no denying the love is there. If you don’t know by now, we’re talking ‘bout Chi-Town. Jump on our Chicago holiday packages like Yeezy jumps on the microphone at awards shows. You won’t be disappointed.

Getting Around Chicago

Chicago flights touch down about 30km northwest of the city centre at O'Hare International Airport (ORD). Just hop on the “L” Blue Line and you’ll be at your hotel before you can say “deepdish pizza”.

When You Land…

Those on early flights to Chicago can hook up with the Lakefront Trail for a morning walk watching the sun rise over the skyline. Better yet, grab a set of two wheels from the city’s bike-sharing system and roll like a local.

You know how Portland and Austin think they’re so “weird”? Well they don’t have the International Museum of Surgical Science, do they? This lakefront goldmine of the oddly captivating has an old-school iron lung, a few lobotomised skulls and a collection of “asthma cigarettes”. Yep, you read that right.

Landing late at night? You’re probably hungry! Book one of our Chicago hotels in the River North neighbourhood so you can drop your stuff before you stuff your face—with deep dish pizza, obviously.

Live Like a Local

If you’re itching to hear people say things like “Lemme get some tips and links”, go north to Wrigleyville. Yes, it’s home to finger-lickin’ BBQ and the famous Wrigley Field, but it’s also got comedy clubs, fantastic bars and a goat curse. Just ask a local about the Curse of the Billy Goat to learn about that last thing.

One thing that definitely isn’t cursed is lastminute.com.au’s awesome selection of cheap flights to Chicago. No need to have a billy goat nearby—just book with us and your holiday is sure to be a home run.

Chicago Flight Deals

What is the cheapest flight to Chicago?

We offer plenty of flight options to Chicago starting at AU$1,333. Sounds like it’s time to book one of the best deals on cheap Chicago flights on lastminute.com.au.

What airlines fly to Chicago?

Each week we have flight options to Chicago. These are some of the most popular airlines with flights to Chicago airports: American Airlines, United, Qantas Airways, Delta, Air Tahiti Nui, Air New Zealand, All Nippon Airways.

At lastminute.com.au, we make it easy to compare cheap flights to Chicago from loads of different airlines. Once you find an itinerary that works for you, booking the flight is as easy as forgetting the bartender’s name after your last drink. There’s no reason to wait—start booking your tickets now, and you’ll be sitting on your suitcase to force it shut in no time.

What are the cheapest days to book a flight?

Looking at lastminute.com.au travel demand in 2021, Wednesdays and Sundays are often the best days to book flights, when prices are generally at their cheapest. You may be tempted to wait to finalise your booking on Saturdays, but our data tells us ticket prices are actually highest on Saturdays. Something to consider when planning your next holiday!

What is the cheapest month to fly?

Here’s the lowdown on the lowest airfares: May is the cheapest month to fly. When looking at 2021 flight demand on lastminute.com.au, flights departing in May generally have the lowest ticket prices. As for the most expensive month to fly, our demand data found that on average, airfares are highest in December.

How far in advance can you book a flight?

Itching to book your dream trip? We totally get it. You can start looking at flights on lastminute.com.au as early as 12 months in advance, but just keep in mind some airlines may not release all their available fares that early. But good news for last minute travellers, with 2021 lastminute.com.au data proving spontaneous travellers can still bag a bargain with some of the cheapest airfares appearing just 1 week prior to travel.

*According to flight demand on lastminute.com.au from January to December 2021. Savings are subject to change and may vary depending on selections made.

Can I fly to Chicago (CHI) on holiday right now?

Make sure your trip to Chicago (CHI) goes smoothly by checking out our Covid-19 Travel Advisor for the lowdown on the current situation.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.