$105 Cheap flight deals from Toronto (YTO) to Chicago (CHI)
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This Weekend's Flight Deals from Toronto to Chicago
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Airfares from $105 One Way, $156 Round Trip from Toronto to Chicago
Prices starting at $156 for return flights and $105 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Chicago economy flight packages
Fairmont Chicago at Millennium Park
Jun 13 - Jun 15
Toronto (YYZ) to Chicago (ORD)
Reviewed on Apr 28, 2025
More About Flying To Chicago from Toronto
Route Information for Flights from Toronto to Chicago
Origin Airport IATA Code | YTO |
|---|---|
Destination Airport IATA Code | CHI |
Distance | 436 mi |
Direct Flight Airlines | American Airlines, Qatar Airways, JAL, Air Canada, EgyptAir, Air New Zealand, United Airlines, Alaska Airlines, Qantas, Finnair, Royal Jordanian, Iberia, ANA, British Airways |
Earliest Flight Arrival | 11:25AM UTC |
Latest Flight Arrival | 2:06AM UTC |
Travel from Toronto to Chicago
Travelers from Toronto often enjoy visiting Chicago for weekend trips or longer vacations to experience the exciting attractions, enlightening cultural events, and incredible shopping opportunities the Windy City has to offer. When planning a trip from Toronto to Chicago, search Orbitz.com for great deals on flights, hotels, and tickets to local attractions.
Leaving Toronto
When heading to Chicago, you'll fly out of Toronto Pearson International Airport, which is located about 17 miles from downtown. Taxis, buses, and the LINK train are all popular ways to get to the airport from central Toronto. Alternately, you can hop on the Express airport shuttle, which makes regular stops throughout the downtown area. If you plan to drive yourself to the airport, you can choose from the value parking garage or the value parking lot, both located just minutes from the terminals on the LINK line.
Visiting Chicago
Chicago has two airports: Chicago O'Hare International Airport and Chicago Midway International Airport. Both airports are served by public buses, and O'Hare has a stop for the CTA Blue line. You can also head into town via taxi or rent a car at the car rental facilities located at both airports. Once in Chicago, check out the Chicago Historical Society museum to get a better idea of the history and culture of the city, then head out to explore. Visit Navy Pier and Lincoln Park Zoo, or relax at Hyde Park before heading out to the theater district to catch a performance. Summer is a popular time to visit Chicago due to the pleasant weather; temperatures average in the low 80s during the day and in the 60s at night. Winters can be cold, with highs near freezing temperature and lows in the 20s, but prices drop significantly during this time.
Your Trip to Chicago
Whether you spend your Chicago vacation investigating the many museums of the city, shopping on the Magnificent Mile, or soaking up culture at local art galleries, you are sure to have a blast in the Windy City. Whatever your vacation budget, check Orbitz.com for great deals on air tickets from Toronto to Chicago, vacation packages, and all of your travel needs.
Frequently asked questions
Flights to Chicago
- New York to Chicago
- Houston to Chicago
- Dallas to Chicago
- Toronto to Chicago
- Phoenix to Chicago
- Los Angeles to Chicago
- Orlando to Chicago
- Las Vegas to Chicago
- San Francisco to Chicago
- Detroit to Chicago
- Washington to Chicago
- New Orleans to Chicago
- Kansas City to Chicago
- Montreal to Chicago
- Sacramento to Chicago
- Hartford to Chicago
- London to Chicago
- Paris to Chicago
- Harrisburg - Hershey to Chicago
- Rome to Chicago
Flights from Toronto
- Toronto to New York
- Toronto to Orlando
- Toronto to Edmonton
- Toronto to Montreal
- Toronto to Los Angeles
- Toronto to London
- Toronto to Dallas
- Toronto to Chicago
- Toronto to Atlanta
- Toronto to Houston
- Toronto to Shanghai
- Toronto to Paris
- Toronto to San Francisco
- Toronto to Washington
- Toronto to Rome
- Toronto to Beijing
- Toronto to Nairobi
- Toronto to New Orleans
- Toronto to Detroit
- Toronto to Buenos Aires
Top Trending
Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.