C$ 178+ 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 22/4. 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 21 March 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 21 March 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 21 March 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
Sun 27/4
3:50 p.m.-4:40 p.m.
Nonstop1h 50m
Chicago Midway
Tue 6/5
9:40 a.m.-12:22 p.m.
Nonstop1h 42m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Wed 16/4
9:00 p.m.-10:06 p.m.
Nonstop2h 06m
Chicago O'Hare Intl
Wed 23/4
12:59 p.m.-3:46 p.m.
Nonstop1h 47m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Fri 2/5
7:55 a.m.-8:45 a.m.
Nonstop1h 50m
Chicago Midway
Sat 3/5
9:40 a.m.-12:22 p.m.
Nonstop1h 42m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Sun 25/5
1:00 p.m.-2:01 p.m.
Nonstop2h 01m
Chicago O'Hare Intl
Fri 30/5
9:35 a.m.-12:15 p.m.
Nonstop1h 40m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Thu 1/5
3:35 p.m.-4:24 p.m.
Nonstop1h 49m
Chicago Midway
Sat 10/5
9:40 a.m.-12:22 p.m.
Nonstop1h 42m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Tue 29/4
1:00 p.m.-2:05 p.m.
Nonstop2h 05m
Chicago O'Hare Intl
Wed 14/5
9:35 a.m.-12:15 p.m.
Nonstop1h 40m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Wed 9/4
11:35 a.m.-12:30 p.m.
Nonstop1h 55m
Chicago O'Hare Intl
Sun 13/4
9:55 a.m.-12:35 p.m.
Nonstop1h 40m
TorontoChicago
YYZ - ORD
YYZORD
Toronto Pearson Intl
Tue 22/4
11:00 a.m.-12:03 p.m.
Nonstop2h 03m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Mon 21/4
9:30 a.m.-10:20 a.m.
Nonstop1h 50m
TorontoChicago
YTZ - MDW
YTZMDW
Toronto Island
Wed 21/5
7:55 a.m.-8:45 a.m.
Nonstop1h 50m
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 21 March 2025.
Entertainment
Crew
Overall
Boarding
Comfort
Food
Reviews
Aaron,Oct 2024
TUS - LAX
Entertainment
Crew
Overall
Boarding
Comfort
Food
Reviews
Aaron,Oct 2024
TUS - LAX
Entertainment
Crew
Overall
Boarding
Comfort
Food
Reviews
Aaron,Oct 2024
TUS - LAX
Entertainment
Crew
Overall
Boarding
Comfort
Food
Reviews
Aaron,Oct 2024
TUS - LAX
Entertainment
Crew
Overall
Boarding
Comfort
Food
Reviews
Aaron,Oct 2024
TUS - LAX
Entertainment
Crew
Overall
Boarding
Comfort
Food
Reviews
Aaron,Oct 2024
TUS - LAX
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).