$98 Cheap Flights from Canada to Chicago
One-way
Departing from
Canada
Going to
Chicago, United States
Chicago (ORD)
United States • October, 2026
86% AI deal score
$340 $107
Chicago (ORD)
United States • September, 2026
86% AI deal score
$340 $106
Chicago (MDW)
United States • May, 2026
84% AI deal score
$290 $98
Chicago (ORD)
United States • November, 2026
83% AI deal score
$340 $107
Chicago (MDW)
United States • May, 2026
82% AI deal score
$290 $98
This is the lowest one-way flight price found by RatePunk users in the last 24 hours for a flight going to Chicago. Fares are subject to change and may not be available for all dates. (Data last updated 4/7/2026).
Popular airlines to Chicago
American Airlines
Air Canada
Alaska Airlines, Inc.
JetBlue Airways
Delta Air Lines
Frontier Airlines
Spirit Airlines
United Airlines
684,505 searches in the past 7 days on RatePunk
Flight deals up to 90% off
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Top Cheap Flight Deals from Canada to Chicago
Recent round-trip flight deals to Chicago
Mon, May 11 - Wed, May 13
Cheapest
Toronto (YTZ) - Chicago (MDW)
Porter Airlines airlines • Direct
Chicago (MDW) - Toronto (YTZ)
Porter Airlines airlines • Direct
$290
$156
-$134
46%
Fri, Jul 24 - Sun, Jul 26
Toronto (YTZ) - Chicago (MDW)
Porter Airlines airlines • Direct
Chicago (MDW) - Toronto (YTZ)
Porter Airlines airlines • Direct
$156
Tue, Jul 7 - Sat, Jul 11
Toronto (YTZ) - Chicago (MDW)
Porter Airlines airlines • Direct
Chicago (MDW) - Toronto (YTZ)
Porter Airlines airlines • Direct
$156
Tue, Jul 7 - Sat, Jul 11
Toronto (YTZ) - Chicago (MDW)
Porter Airlines airlines • Direct
Chicago (MDW) - Toronto (YTZ)
Porter Airlines airlines • Direct
$156
Thu, Jul 30 - Sun, Aug 2
Toronto (YTZ) - Chicago (MDW)
Porter Airlines airlines • Direct
Chicago (MDW) - Toronto (YTZ)
Porter Airlines airlines • Direct
$157
Thu, Jul 30 - Sun, Aug 2
Toronto (YTZ) - Chicago (MDW)
Porter Airlines airlines • Direct
Chicago (MDW) - Toronto (YTZ)
Porter Airlines airlines • Direct
$157
The cheapest time to fly to Chicago
Ready to jet to Chicago on a budget? Check out these popular routes with surprisingly cheap fares (one-way prices):
Facts About Flights from Canada to Chicago
To help you plan your journey, here are some quick Chicago flight facts and tips.
Chicago city airports
Chicago is a major transportation hub with several airports serving the region. The two primary airports are O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW). O'Hare, one of the busiest airports in the world, is located on the northwest side of Chicago and serves as a major hub for United Airlines and American Airlines, offering extensive domestic and international routes. Midway, located on the southwest side of the city, is a major base for Southwest Airlines and provides primarily domestic flights. A third option is Chicago Rockford International Airport (RFD), located about 85 miles northwest of Chicago. While farther away, RFD can be a convenient alternative, especially for travelers in northern Illinois or southern Wisconsin, and it's known for its cargo operations and passenger service from low-cost carriers.
O Hare International (ORD)
Chicago, United States
Chicago Midway International (MDW)
Chicago, United States
Chicago Rockford International (RFD)
Chicago, United States
Pro tip: search “Chicago (Any)” to see fares to all Chicago airports – sometimes one is cheaper than the others on your dates.
Insights for flights to Chicago
Cheapest airport
Chicago Midway (MDW)
Chicago Midway International Airport (MDW) is often the most budget-friendly option for your trip to the Windy City. Located closer to downtown than O'Hare, Midway offers a convenient and less chaotic experience, especially if you're looking to quickly dive into Chicago's famous deep-dish pizza scene.
Nonstop vs. 1-stop
100+ cities
As a major hub, Chicago acts as a connection point to over 100 cities with popular routes to both coasts, making cross-country travel a breeze.
Number of airlines
50+ airlines
Chicago is a major aviation hub served by over 50 airlines, so you'll have a plethora of options to choose from to reach your destination! Popular choices include full-service carriers like United and American Airlines, as well as budget-friendly options such as Southwest and Spirit.
Typical price range (round-trip)
Flights to Chicago: Unbeatable Deals Await! ($75 - $450)
Dreaming of deep-dish pizza and dazzling skyscrapers? Flights to Chicago typically range from $75 to $450, but prices can fluctuate. Keep an eye out for higher fares during summer and around the holidays, when everyone flocks to the Windy City. Consider flying during the shoulder seasons (spring or fall) for potentially better deals!
Flight frequency
2,000+ flights
Flights to Chicago are available daily, with increased frequency during the summer months and around major holidays. You'll find the most options during peak travel times!
ORD Airport Deal Stats
Current most discounted routes
Avg. most discounted routes (last 3 months)
ORD airport insights
Best days to catch a deal
Wed, Tue
Based on the provided data, Saturday has the highest probability of finding the cheapest deals for flights from O'Hare International Airport. Sunday is also a good day to check for deals.
Avg. deal survival time
19.0 hours
Deals from O'Hare International Airport survive for an average of 19.0 hours. Be sure to book quickly as deals can disappear fast!
Rare deal frequency
19 deals
We found 19 rare deals for flights in and out of O'Hare International Airport in the past month, with each deal having an AI Deal Score of 90 or higher. These rare deals are typically mistake fares, special promotions, or ultra-discounts.
Average price drop
-70%
The average price drop for flights arriving at O'Hare International Airport is 70.1%, indicating a significant potential for savings. This suggests that travelers flying into O'Hare could benefit from monitoring price fluctuations and booking when prices are lower.
Next 4 weeks: deal forecast
O'Hare International Airport Next Month Forecast
Based on current trends, flight prices to O'Hare International Airport are expected to slightly increase next month. There are no significant price drops anticipated, so booking in advance is recommended to secure the best deals.
Top 5 biggest price drops (last 3 months)
Found on April 1
Columbus - ORD
$2,825 → $149
95%
Found on March 27
Mount Hagen - ORD
$7,750 → $963
88%
Found on March 27
Paderborn - ORD
$3,400 → $460
86%
Found on March 27
Twin Falls - ORD
$700 → $111
84%
Found on April 1
Cancún - ORD
$645 → $147
77%
Check these nearby airports too
Looking for more options? These airports near ORD sometimes drop rare deals too:
Gerald R. Ford International (GRR)
~12 rare deals/month
General Mitchell International (MKE)
~14 rare deals/month
Chicago Rockford International (RFD)
~14 rare deals/month
If you’re flexible with departure cities, it’s worth keeping an eye on nearby airports — especially GRR and MKE for long-haul deal surprises.
When Is the Best Time to Fly from Canada to Chicago
Timing is everything when hunting for cheap flights. Here are data-backed insights on the best times to fly to Chicago:
Cheapest month
January
Cheapest month
January is typically the cheapest month to fly to Chicago. The city is covered in snow, creating a beautiful winter wonderland. You can often find great deals on flights and hotels during this time, as it's after the holiday rush and before spring break season.
Best day to book
Tuesday
Best day to book
Tuesday is often the best day to book a flight to Chicago. Airlines tend to release new deals early in the week. Keep an eye out for flash sales and limited-time offers on Tuesdays to snag the best prices for your trip to the Windy City!
Cheapest days to fly
Wednesday
Cheapest days to fly
Flights on Wednesdays are often cheaper than on other days of the week. Mid-week travel tends to be less popular, leading to lower demand and better deals. Flying on a Wednesday can help you save some serious cash, leaving you more to spend on deep-dish pizza.
Advance booking sweet spot
2 months
Advance booking sweet spot
Booking about 2 months in advance is often the sweet spot for flights to Chicago. Airlines adjust prices based on demand as the travel date approaches. Booking a couple of months out can help you avoid last-minute price hikes and secure a better deal for your trip.
Seasonal considerations
Distinct
Seasonal considerations
Chicago experiences distinct seasonal changes, which significantly impact flight prices. Summer is peak season, with higher prices due to warmer weather and festivals. Winter sees lower prices, but be prepared for potential weather-related delays.
TL;DR: January is the cheapest month to fly to Chicago, offering a snowy cityscape and budget-friendly travel. Tuesdays are prime for booking flights due to airline deals, while flying on a Wednesday can save you money. Aim to book about 2 months in advance for the best prices. Keep in mind Chicago's distinct seasons, as summer is pricier and winter may bring weather-related disruptions.
Chicago Airports & Ground Transportation
One big question for travelers is which Chicago airport to fly into. Here’s a quick guide to Chicago’s airports and how to get to the city from each:
Chicago O'Hare International Airport (ORD)
O'Hare International Airport is one of the busiest airports in the world, serving as a major hub for United and American Airlines. With four terminals and numerous concourses, it offers a wide variety of dining, shopping, and lounge options to keep travelers comfortable. Located about 17 miles northwest of downtown Chicago, O'Hare is easily accessible via the 'L' train's Blue Line, offering a direct and affordable connection to the city center. The airport is known for its sometimes long walks between gates, so wear comfortable shoes! Don't be surprised to spot a plane taking off, it happens every minute!
Tip: Give yourself plenty of time to navigate this massive airport, especially if you have connecting flights.
Chicago Midway International Airport (MDW)
Midway International Airport, located on the southwest side of Chicago, is a convenient option for travelers seeking a closer alternative to O'Hare. It is a major hub for Southwest Airlines and provides a more streamlined and less overwhelming experience compared to its larger counterpart. The airport offers a selection of restaurants, shops and amenities. Getting downtown is a breeze, just hop on the 'L' train's Orange Line for a direct ride into the heart of the city. Perfect for a quick getaway!
Tip: Midway's smaller size means shorter walks, but it can get crowded, so arrive early.
Other airports
Okay, so Chicago is great, but sometimes the best flight deals land a bit outside the city! Airports like Milwaukee (MKE) and South Bend (SBN) can offer cheaper flights, but remember to factor in the commute to Chicago. Milwaukee is about 90 miles north, and South Bend is about 95 miles east, so plan for a bus, train or rideshare to get you to the Windy City.
Airport transfers
Getting around Chicago from its airports is a breeze with a variety of options! Public transportation via the 'L' train is super affordable, while taxis and rideshares offer door-to-door service at a higher price. For those who prefer to drive, rental cars are readily available, just be mindful of Chicago's traffic!
What to Do in Chicago
Chicago isn’t just about getting there – it’s about enjoying the country once you arrive! Here are some top things to do in Chicago, organized by interest:
Sightseeing & landmarks
Chicago is a city brimming with iconic landmarks! Make sure you visit Cloud Gate (aka "The Bean") in Millennium Park, ascend the Willis Tower for breathtaking views, and stroll along the scenic Riverwalk. Don't forget to check out the historic Water Tower and the beautiful architecture on display during a river cruise!
Arts & culture
Chicago's art scene is vibrant and diverse. Explore world-class institutions like the Art Institute of Chicago, catch a Broadway-quality show in the Theater District, and immerse yourself in the city's many colorful murals and public art installations. Be sure to check out a blues or jazz club for a taste of Chicago's musical heritage!
Food & nightlife
Get ready for a culinary adventure in Chicago! From deep-dish pizza to gourmet dining, the city offers something for every palate. Explore the diverse neighborhoods for authentic ethnic cuisine, and experience the lively nightlife scene, from trendy cocktail bars to blues clubs.
Shopping & fashion
Shop 'til you drop on the Magnificent Mile, Chicago's premier shopping destination! Discover high-end boutiques, department stores, and unique shops. Explore the trendy neighborhoods like Wicker Park and Bucktown for independent boutiques and vintage finds.
Nearby getaways
Escape the city for a day trip to one of Chicago's charming nearby destinations. Explore the beautiful beaches and dunes of Indiana Dunes National Park, visit the historic town of Galena, or head to Milwaukee to explore the breweries. These quick getaways offer a refreshing change of pace!
No matter your interest – be it art, food, nightlife, or nature – Chicago has something for everyone. And the best part? Many events and attractions refresh throughout the year, so there’s always something new to experience each visit.
Events in Chicago This Month
in the key of 3
City Winery Chicago, PUSH 365, and TrustLive Entertainment present In The Key of 3, featuring Joyce Hurley, Simbryt, and Simone Green live on Tuesday, March 31st at 7:30 PM. This is a night of incredible music and entertainment you won't want to miss.
catchlight
In partnership with ONA, the largest journalism conference in the country, and Borderless Magazine, this program features live storytelling by John Moore (Getty Images) and Camilla Forte, sharing powerful narratives and insights.
cards and conversation
Join us for an evening of card games, board games, and engaging conversation. All are welcome, especially new faces looking to connect and have some fun!
the posthumous trial of giulia tofana
Giulia Tofana is remembered as a murderer, poisoner, and witch, Italy’s most prolific serial killer and the infamous creator of the Aqua Tofana poison. Authorities pursued her for her deadly craft, shrouded in mystery and intrigue.
megan from work
Find tickets to see Guardrail perform live at Lemon in Chicago on March 31, 2026, at 7:30 PM. Experience an unforgettable night of music and energy.
Chicago Weather
Weather in Chicago
Tue, Mar 31
75%
21° 2°
75%
Wed, Apr 1
10%
5° 2°
10%
Thu, Apr 2
75%
19° 5°
75%
Fri, Apr 3
35%
16° 7°
35%
Sat, Apr 4
40%
13° 2°
40%
Sun, Apr 5
10%
8° 1°
10%
Mon, Apr 6
20%
10° -1°
20%
Here’s a quick look at the weather you can expect, plus this week’s forecast:
Seasons: Chicago experiences four distinct seasons. Spring (March-May) brings increasing temperatures from 2.2°C to 21.4°C (36°F to 71°F) with frequent rain. Summer (June-August) is warm, averaging 20°C to 30°C (68°F to 86°F). Autumn (September-November) sees temperatures drop from 20°C to 5°C (68°F to 41°F) with colorful foliage. Winter (December-February) is cold, averaging -5°C to 5°C (23°F to 41°F), with snow.
Rain: Precipitation in Chicago includes both rain and snow. Rain is common in spring and fall, while snow typically occurs from late fall to early spring. While impactful to travel at times, the city is well-equipped to handle these conditions.
This week's forecast: The weather forecast for this week in Chicago (March 31 - April 6, 2026) shows a mix of conditions. Temperatures range from -0.7°C to 21.4°C (31°F to 71°F), with rain expected on several days and a chance of snow around April 5th and 6th. Expect variable weather with both warm and cold spells.
(We update the weather forecast weekly so you know what to expect during your travel week. Always check a day or two before your flight for the most current conditions.)
Frequently Asked Questions About Flights to Chicago
(Have more questions?) Feel free to reach out or check our comprehensive Chicago travel guide. We’re here to help make your flight to Chicago (and the trip itself) as smooth as possible.
Pro Tips for Finding Cheap Flights to Chicago
Finally, to wrap up, here’s a cheat sheet of pro tips that experienced travelers use to save on Chicago flights:
Be Flexible With Your Dates: Sometimes flying on a Tuesday or Wednesday can save you serious dough compared to weekends. Play around with your dates to see the cheapest options – think of it as a fun game of travel Tetris!
Consider Alternative Airports: Chicago has two main airports: O'Hare (ORD) and Midway (MDW). Flying into one versus the other can drastically change the price, so compare both to snag the best deal.
Snatch Those Early Bird (or Late Night) Deals: Airlines often release deals at odd hours, so set those alarms or browse late at night. You might just find a fare so good, it feels like you're dreaming!
Embrace the Art of the Layover: Non-stop flights are nice, but flights with layovers are often cheaper. If you're not in a rush, embrace the layover and save some cash for deep-dish pizza!
Use Incognito Mode Like a Secret Agent: Airlines might track your searches and raise prices, so browse in incognito mode to keep them guessing. Think of it as your travel superpower!
Bundle Up! (Flights and Accommodation): Sometimes booking your flight and hotel together can unlock hidden discounts. It's like a travel combo meal – more for less!
Loyalty Programs: Your Ticket to Savings: Join airline loyalty programs to earn points and miles. These can lead to free flights, upgrades, and other perks. Start racking up those rewards!
Follow Airlines on Social Media: Airlines often announce flash sales and special deals on their social media channels. Stay in the loop to catch those fleeting offers!
Set Up Price Alerts with RatePunk: Let RatePunk do the work for you! Set up price alerts for your desired dates and destination, and RatePunk will notify you when the price drops. Never miss a deal again!
Consider Budget Airlines: Budget airlines can offer incredibly low fares, but be sure to factor in extra costs for baggage, seat selection, and snacks. Sometimes basic is brilliant!
By keeping these tips in mind, you’ll be well-equipped to find the cheapest flights to Chicago and make the most of your travel budget. After all, the more you save on your flight, the more you can spend on a Broadway show, a nice meal, or an extra tour in Chicago! 🎉✈️