C$ 166+ Direct flights to Chicago
This is the cheapest price on a non-stop flight to Chicago found by a Cheapflights user in the last 72 hours by searching for a flight departing on 25/6. Fares are subject to change and may not be available on all flights or dates of travel.
Find flight deals to Chicago
Cheapest flights to ChicagoExplore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 29 April 2025.
Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 29 April 2025.
Best time to book a flight to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago with our price prediction graph.
Cheapflights Fare Finder
Use the slider to find non-stop flights to Chicago within your budget. Price data is based on user searches made on Cheapflights. Over the past seven days, Cheapflights users made 629,999 searches and data was last updated on 29 April 2025.
Use the filters below to find and compare direct flights to Chicago that are best for you.
Fly from
Route
Depart
Return
Price
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Fri 6/6
3:35 p.m.-4:24 p.m.
Nonstop1h 49m
Chicago Midway
Mon 9/6
5:50 p.m.-8:32 p.m.
Nonstop1h 42m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 28/8
7:55 a.m.-8:45 a.m.
Nonstop1h 50m
Chicago Midway
Mon 1/9
9:15 a.m.-11:57 a.m.
Nonstop1h 42m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 6/6
11:00 a.m.-12:01 p.m.
Nonstop2h 01m
Chicago O'Hare Intl
Sun 8/6
7:04 a.m.-9:58 a.m.
Nonstop1h 54m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 10/7
3:35 p.m.-4:24 p.m.
Nonstop1h 49m
Chicago Midway
Sun 13/7
5:20 p.m.-8:02 p.m.
Nonstop1h 42m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Mon 21/7
2:10 p.m.-3:04 p.m.
Nonstop1h 54m
Chicago O'Hare Intl
Fri 25/7
8:25 p.m.-11:10 p.m.
Nonstop1h 45m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 22/5
1:00 p.m.-2:01 p.m.
Nonstop2h 01m
Chicago O'Hare Intl
Wed 28/5
5:55 p.m.-8:44 p.m.
Nonstop1h 49m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Tue 27/5
3:10 p.m.-4:05 p.m.
Nonstop1h 55m
Chicago O'Hare Intl
Tue 3/6
8:11 a.m.-10:51 a.m.
Nonstop1h 40m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 30/5
1:15 p.m.-2:10 p.m.
Nonstop1h 55m
Chicago O'Hare Intl
Sun 1/6
8:11 a.m.-10:51 a.m.
Nonstop1h 40m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 22/5
2:10 p.m.-3:05 p.m.
Nonstop1h 55m
Chicago O'Hare Intl
Sun 25/5
8:25 p.m.-11:07 p.m.
Nonstop1h 42m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Wed 25/6
3:35 p.m.-4:24 p.m.
Nonstop1h 49m
Reviews of airlines flying non-stop to Chicago
Get insights into the airlines that provide direct flights 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 29 April 2025.
Overall
Crew
Entertainment
Boarding
Food
Comfort
Reviews
Anonymous,Apr 2025
MCO - YHZ
Overall
Crew
Entertainment
Boarding
Food
Comfort
Reviews
Anonymous,Apr 2025
MCO - YHZ
Overall
Crew
Entertainment
Boarding
Food
Comfort
Reviews
Anonymous,Apr 2025
MCO - YHZ
Overall
Crew
Entertainment
Boarding
Food
Comfort
Reviews
Anonymous,Apr 2025
MCO - YHZ
Overall
Crew
Entertainment
Boarding
Food
Comfort
Reviews
Anonymous,Apr 2025
MCO - YHZ
Overall
Crew
Entertainment
Boarding
Food
Comfort
Reviews
Anonymous,Apr 2025
MCO - YHZ
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).