Cheap flights to Chicago from $1,057
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 22/5. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
Flights to Chicago in 2024
Find the latest flights to Chicago in 2024, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 525,180 searches and data was last updated on 14 May 2024.
Cheap flights to Chicago in May & June 2024
Discover affordable flights and deals to Chicago in May and June 2024. In the last 7 days, Cheapflights users made a total of 525,180 searches and data was last updated on 14 May 2024.
Check out some of the flights available from low prices to Chicago in May and June 2024. Deals update frequently so be sure to check back soon if you're not finding what you're looking for.
Chicago 2024 flight deals
Explore flight deals for Chicago in 2024, offering the best prices and options to suit your preferences. In the last 7 days, Cheapflights users made a total of 525,180 searches and data were last updated on 14 May 2024.
The lowest fares on flights travelling to Chicago in May and June 2024. Check back in a little while for more flight options.
Flights to Chicago departing soon
Discover available last-minute flight options to Chicago, providing immediate availability and potentially lower prices. In the last 7 days, Cheapflights users made a total of 525,180 searches and data was last updated on 14 May 2024.
Users travelling to Chicago last-minute should check out these flights departing soon. Tip: double check your flight details before making your reservation.
One-way flights to Chicago
Explore one-way flight options to Chicago for greater flexibility in your travel plans. Find up-to-date pricing and availability for one-way flights. In the last 7 days, Cheapflights users made a total of 525,180 searches and data was last updated on 14 May 2024.
If you're looking for options on one-way flights to Chicago, check out these fares. Those seeking round-trip flights to Chicago should utilize the search form at the top of the page.
Find flights to Chicago within your budget
Locate flights to Chicago that fit your budget, with regularly updated fares and availability. In the last 7 days, Cheapflights users made a total of 525,180 searches and data was last updated on 14 May 2024.
Fly from
Budget
$1,335 - $1,786
Route
Depart
Return
Price
Sydney Kingsford SmithChicago O'Hare Intl
SYD - ORD
SYDORD
Sydney Kingsford Smith
Wed 12/6
2 stops34h 15m
Chicago O'Hare Intl
Wed 19/6
1 stop32h 50m
Sydney Kingsford SmithChicago O'Hare Intl
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 31/10
1 stop33h 47m
Chicago O'Hare Intl
Sun 3/11
1 stop21h 32m
Sydney Kingsford SmithChicago Midway
SYD - MDW
SYDMDW
Sydney Kingsford Smith
Thu 31/10
2 stops39h 12m
Chicago Midway
Sun 3/11
2 stops45h 20m
Sydney Kingsford SmithChicago O'Hare Intl
SYD - ORD
SYDORD
Sydney Kingsford Smith
Wed 12/6
2 stops31h 34m
Chicago O'Hare Intl
Wed 19/6
3 stops32h 13m
Sydney Kingsford SmithChicago O'Hare Intl
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 24/10
1 stop25h 36m
Chicago O'Hare Intl
Sat 16/11
2 stops33h 00m
Sydney Kingsford SmithChicago O'Hare Intl
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 24/10
1 stop26h 55m
Chicago O'Hare Intl
Thu 14/11
2 stops44h 05m
Sydney Kingsford SmithChicago O'Hare Intl
SYD - ORD
SYDORD
Sydney Kingsford Smith
Mon 24/6
1 stop34h 27m
Chicago O'Hare Intl
Wed 3/7
1 stop20h 20m
Sydney Kingsford SmithChicago O'Hare Intl
SYD - ORD
SYDORD
Sydney Kingsford Smith
Thu 10/10
1 stop21h 21m
Chicago O'Hare Intl
Tue 15/10
1 stop21h 45m
Sydney Kingsford SmithChicago O'Hare Intl
SYD - ORD
SYDORD
Sydney Kingsford Smith
Fri 11/10
2 stops28h 55m
Chicago O'Hare Intl
Fri 18/10
2 stops24h 04m
Average price of flights to Chicago by month
Plan your trip to Chicago by taking into account the cheapest months to travel. The average price of a one-way flight to Chicago is currently $1,287 while a return flight costs $1,602. Price data was last updated on 12 May 2024.
Currently, February is the cheapest month in which you can book a flight to Chicago (average of $928). Flying to Chicago in December will prove the most costly (average of $1,591). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.
January
$1,648
February
$1,403
March
$1,594
April
$1,875
May
$1,763
June
$1,795
July
$1,929
August
$1,914
September
$1,743
October
$1,687
November
$1,940
December
$2,406
Chicago’s seasons are intense – it’s hot in the summer and cold in the winter – but savvy travellers can always find cheap flights to Chicago.
Peak Season
Summer is between June and August and it is the peak of the festival season in the Chicago area with major events taking place in the parks and neighbourhoods every weekend, in spite of the heat and humidity from the Lake. Taste of Chicago, taking place mid-July at the lakefront is an outdoor food festival which showcases the variety of cuisines and local flavours accompanied by live music. Cheap flights to Chicago are more difficult to find during this popular festival. August is host to another popular event – the Chicago Air and Water Show. With free admission and lakefront location, the show attracts huge numbers of fans of aviation and adventure seekers.
September can be the most enjoyable and mild month of the year but there’s less going on during this period.
Off-Peak Season
January to March is least busy making cheap flights to Chicago and hotel deals attainable. However, true to its reputation as the “Windy City”, cold temperatures and brisk winds will make you want to stay inside for most of your visit.
Temperature and rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average temperature and rainfall totals by month.
CHI Temperature | -5 - 23 °C |
|---|
If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).
When is the best time to book a flight to Chicago?
Use this chart to determine the optimal time to book a return flight to Chicago. Price data was last updated on 10 May 2024.
Booking 35 days in advance of your planned departure date is, on average, the best time to get cheap flights to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
When is the cheapest time to fly to Chicago?
Use this chart to determine the cheapest time to fly return to Chicago. Price data was last updated on 12 May 2024.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 14 May 2024.
Read through reviews of airlines servicing Chicago, such as United Airlines, American Airlines and Virgin Australia. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
Comfort
Food
Entertainment
Overall
Crew
Reviews
Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Boarding
Comfort
Food
Entertainment
Overall
Crew
Reviews
Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Boarding
Comfort
Food
Entertainment
Overall
Crew
Reviews
Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Boarding
Comfort
Food
Entertainment
Overall
Crew
Reviews
Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Boarding
Comfort
Food
Entertainment
Overall
Crew
Reviews
Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Boarding
Comfort
Food
Entertainment
Overall
Crew
Reviews
Les sièges sont étroits, je mesure 1,77 m, les passants dans le couloirs notamment l'équipage n'arrêtaient pas de me cogner. nous étions en économie. l'équipage est au top. C'est le confort qui était négatif pour nous.
Why Visit
Chicago is a skyscraper metropolis and a feat of modern architecture as well as home to what was once the world’s tallest building, Sears Tower. Chicago may not be a traditional tourist destination but you will find that the Second City is well worth a visit. As the hub of the Midwest, Chicago is not to be overlooked. Its picturesque skyline is reflected in the waters of Lake Michigan. World-class museums of art and science, fine public art, huge parks and sandy beaches and a multicultural vibe (thanks to the Poles, the Italians, the Greeks and the Irish among many other groups) make it an unbeatable destination for a holiday. First stop should be the lakefront, from Lakeview to Oak Street Beach, the entire area is bustling for things for you to do and to see. Take a cheap flight to Chicago and the city will match your passion.
Chicago has long been thought of as the nation’s second city – indeed, Chicagoans only grudgingly admit that New York occupies first place. The city’s central area, including the Loop and the Magnificent Mile, is famous for its combination of modern and historic architecture. Chicago is also home to many of the country’s best museums and art galleries, including the Field Museum of Science and Industry and, reflecting the city’s industrial heritage, the Museum of Science and Industry.
Getting around Chicago
Chicago’s regular, grid-like layout makes navigation straightforward, but the “City With Big Shoulders” can be a little too large to get around easily on foot. Fortunately, the city’s public transportation system, including the famous “L” (short for “elevated train tracks”), is efficient, with especially good coverage in the city centre area. Traffic is often congested, especially during rush hour, and driving isn’t recommended. Cycling is a popular way to get around and with all of Chicago’s lakefront property, it can be a great way to enjoy the city.
Getting downtown from the airport
Chicago’s major airport is O’Hare International Airport (ORD) located in the city’s northwest corner, about 27 km away from the Loop. The Blue Line of the Chicago subway (known as the ‘L’ to locals) connects O’Hare directly to the city, and commuter rail services are easily accessible by a short shuttle ride. Taxi and car hire services are also available.
Travel Tips
One of the biggest challenges for visitors to Chicago can be the weather. Fiercely hot in the summer, the city is bitterly cold and windy in the winter. In the winter, wear layers and don’t expose skin to the wind; in summer, be sure to drink plenty of water.