Cheap flights to Chicago from C$ 177
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 1/7. 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 407,867 searches and data was last updated on 18 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 407,867 searches and data was last updated on 18 May 2024.
The below flights offer some of the lowest fares to Chicago in May and June 2024. Be sure to check back soon as deals update often.
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 407,867 searches and data were last updated on 18 May 2024.
Listed are some of the best fares we've found on flights departing to Chicago in 2024. If these deals don't appeal to you, be sure to come back soon for more 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 407,867 searches and data was last updated on 18 May 2024.
Browse some of the best deals on flights leaving last minute to Chicago. 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 407,867 searches and data was last updated on 18 May 2024.
Take a look at some of the one-way flights departing to Chicago in the near future. Reserve a round-trip flight to Chicago instead by utilizing the search form above.
Direct flights to Chicago
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 407,867 searches and data was last updated on 18 May 2024.
Fly from
Budget
C$ 297 - C$ 652
Route
Depart
Return
Price
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Mon 9/9
Nonstop1h 47m
Chicago Midway
Thu 12/9
Nonstop1h 42m
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Mon 3/6
Nonstop1h 47m
Chicago Midway
Thu 6/6
Nonstop1h 42m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Mon 1/7
Nonstop1h 56m
Chicago O'Hare Intl
Tue 16/7
Nonstop1h 43m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 31/5
Nonstop1h 56m
Chicago O'Hare Intl
Sat 1/6
Nonstop1h 43m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 25/7
Nonstop1h 57m
Chicago O'Hare Intl
Tue 30/7
1 stop6h 07m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sat 1/6
Nonstop1h 55m
Chicago O'Hare Intl
Thu 13/6
Nonstop1h 50m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 31/5
1 stop4h 29m
Chicago O'Hare Intl
Wed 5/6
1 stop8h 14m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sun 16/6
1 stop4h 17m
Chicago O'Hare Intl
Mon 17/6
1 stop5h 53m
Toronto Pearson IntlChicago Midway
YYZ - MDW
YYZMDW
Toronto Pearson Intl
Mon 17/6
1 stop8h 19m
Chicago Midway
Thu 20/6
1 stop18h 26m
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 C$ 183 while a round-trip flight costs C$ 375. Price data was last updated on 12 May 2024.
Currently, January is the cheapest month in which you can book a flight to Chicago (average of C$ 261). Flying to Chicago in August will prove the most costly (average of C$ 440). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.
January
C$ 356
February
C$ 414
March
C$ 441
April
C$ 454
May
C$ 477
June
C$ 550
July
C$ 591
August
C$ 599
September
C$ 466
October
C$ 508
November
C$ 460
December
C$ 475
Peak Season:
Summer runs from June through August and is a hugely popular time in the city, despite the heat and humidity from the Lake. This is also the Chicago’s peak festival season, which sees major events taking place in the parks and neighbourhoods every weekend. Prices for flights to Chicago and crowd numbers can see an increase when the city hosts its most popular festivals.
Foodies should book a flight to Chicago during mid-July for the Taste of Chicago festival. This outdoor food event takes place at the lakefront and showcases a variety of cuisines and local flavours accompanied by live music. 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 when Chicago is least busy, making cheap flights to Chicago and hotel deals more 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 round-trip flight to Chicago. Price data was last updated on 10 May 2024.
To ensure you get the cheapest price possible for a flight to Chicago, you should look to book at least 37 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
When is the cheapest time to fly to Chicago?
Use this chart to determine the cheapest time to fly round-trip 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 18 May 2024.
Get a feel of what it's like to fly with WestJet, Air Canada and United Airlines to Chicago by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
Comfort
Overall
Crew
Boarding
Entertainment
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Food
Comfort
Overall
Crew
Boarding
Entertainment
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Food
Comfort
Overall
Crew
Boarding
Entertainment
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Food
Comfort
Overall
Crew
Boarding
Entertainment
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Food
Comfort
Overall
Crew
Boarding
Entertainment
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.
Food
Comfort
Overall
Crew
Boarding
Entertainment
Reviews
When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.