Miles and miles of magnificence.
With non-stop flights from Toronto to Chicago, you’ll experience a city that’s bustling and full of energy all year round. With top notch cultural attractions, famous neighbourhoods, and architectural awes at every turn, it’s fun to go around and explore all the gems that Chicago offers.
The Windy City has plenty of iconic attractions you have to try when flying from Toronto. Chomp down on Chicago’s own deep-dish pizza, take a stroll down the Magnificent Mile, catch a baseball game at Wrigley Field, wander through Millennium Park, or take in history and art at Chicago’s long list of museums and art galleries. With endless activities and places to see, you’ll never run out of entertainment with a flight to Chicago from Toronto.
Experience Chicago’s diversity when you journey into the city’s neighbourhoods and experience a wide brush stroke of artistic areas, stroller-friendly sanctums, big-block stores, and charming boutique districts. Find an eclectic mix of both tourists and friendly locals along the way that will surely brighten your day. You’ll look forward to another trip to Chicago from Toronto.
From awesome attractions to noteworthy neighbourhoods, daily flights from Toronto to Chicago will have you enjoying this diverse city in no time.
Wicker Park
A welcome home to hip businesses and creative crowds.
After your flight from Toronto to Chicago lands, discover Wicker Park, a recently-revitalized neighbourhood near the downtown core.
This neighbourhood saw an energetic change in the mid-19th century, when the Rolling Mill steelworks opened and employed a wave of Irish labourers. Just a century and a half later, a diverse mix of communities call this neighbourhood home.
The empty warehouses and affordable loft spaces have sparked the most recent demographic shift, causing a wave of artists and white-collar professionals to flood into the area. Today, young families, creative types, and entrepreneurs mingle in this diverse neighbourhood, distinguished by its rich assortment of independently-owned shops, restaurants, and galleries.
This diverse neighbourhood boasts some of the most sought after places to eat. The area is also known for its palate-pleasing nightcaps and cool breweries for visitors to indulge in. With Wicker Park’s award-winning dining experience, flights to Chicago from Toronto are sure to satisfy your hunger.
Looking for some fun things to do in Wicker Park? Retail therapy is a great option in this neighbourhood. Discover vintage shops and independently-owned fashion boutiques for the on-trend shoppers along the northern division, on Milwaukee and Damen Avenue. The shopping doesn’t end there, the area also includes a large mix of big-name stores on the same block to satisfy all types of shoppers.
Channel your inner creative, satisfy your hunger, and shop until you drop when you visit Wicker Park with a flight from Toronto to Chicago.
Logan Square
Venture off the eaten path.
Be sure to add Logan Square to your Chicago travel itinerary. Refined cafes, galleries, trendy bars and boutiques have sprung up along the neighborhood's boulevards, lined with tall sycamore trees - there truly is something for everyone in the Logan Square neighborhood!
Logan Square is big on supporting locals. Renowned restaurants, neighborhood bars and breweries make the most of local ingredients. Galleries showcase the works of local artists of all ages, and emerging groups headline concerts and festivals. Fly from Toronto to Chicago and experience what this vibrant neighborhood offers for yourself.
Known for its architecture, ethnic diversity and a strong community that warmly welcomes newcomers with an entrepreneurial spirit, the neighborhood is built around Logan Square where the towering Illinois Centennial Monument stands.
The heart of the neighborhood is located in the square traced by Kedzie and Logan boulevards, at the Milwaukee Avenue roundabout. This area is part of Chicago's Emerald Necklace, a network of parks and urban landscapes. In the summer, you can admire the greenery and large trees that line these picturesque streets.
You’ll love Logan Square’s atmosphere and its numerous restaurants and activities when you fly from Toronto to Chicago!
How to get to Billy Bishop Toronto City Airport (YTZ)
Porter’s check-in desk is located on the second floor, in the departures area.
Billy Bishop Toronto City Airport (YTZ) is about 3 km / 2 mi from downtown Toronto.
Transportation to Billy Bishop Toronto City Airport
All roads and rails lead to Porter. Located at the base of Bathurst Street, Billy Bishop Toronto City Airport is easily accessible by streetcar (the 511 streetcar via Bathurst subway station and the 509 streetcar via Union Station). You can take the subway, GO Transit, PATH or UP Express to and from Union Station and then hop on the free shuttle bus service to get you to Porter as well.
Ride-hailing apps Uber and Lyft are available for pick-up and drop-off at the airport.
Please allow sufficient time to drop off your car rental before your departing flight.
Taxis from downtown cost about $10 CAD. Car service is about $40 CAD.
The shuttle pick-up and drop-off location downtown is by the west entrance of the Royal York Hotel on York Street.
The shuttle bus offers comfortable and complimentary service between downtown and Billy Bishop Toronto City Airport, approximately every 15 minutes. Times may vary due to traffic and road conditions.
You can choose to take the pedestrian tunnel to Billy Bishop Toronto City Airport or the 90-second ferry ride that runs every 15 minutes across Toronto’s inner harbour.
The UP Express Train connects you between Union Station, Bloor Station, Weston Station and Pearson Airport. For ticket fares and schedules, visit upexpress.com
Billy Bishop Toronto City Airport (YTZ) Parking
Offsite parking is available at the Queens Quay West location in a bright, clean, eight-story parking facility with 1,100 parking spaces available to passengers 24 hours a day, 7 days a week. The facility is monitored by a security team, and is equipped with video surveillance to provide a safe environment for the guests. The daily rate is $15 when prebooked, and free shuttle runs to and from the airport.
The information and figures above are for reference only, and may not be current. Please visit each airport's website for up-to-date details.
Chicago Midway Airport Transportation to Downtown
There are many options for transportation to downtown Chicago from Chicago Midway International Airport (MDW).
The trip is about 9 km / 6 mi from the airport to downtown Chicago.
Transportation to downtown Chicago
The Go Airport Express shuttle bus provides service from the airport to downtown Chicago. Reservations can be made online and fares start at $23 USD.
Uber and Lyft pickup is available at Chicago Midway Airport. To find your ride, exit at the baggage claims level, exit through door 4, and cross the street. Fares from MDW to downtown Chicago start at $23.
Car rental services are available at Chicago Midway Airport (MDW). Take the shuttle to the rental car area from the pick-up location at door 3 of the lower level, near the baggage claim area.
Taxis to downtown cost about $29 USD per person. Car service is available.
Take the Chicago Transit Authority orange line train from the Midway stop. The fare is $2.50 USD.
Chicago Midway International Airport Parking
Driving to Chicago Midway International Airport? There are many parking options at Chicago Airport. There are two economy parking lots with a rate of $2 USD for 30 minutes, $5 USD for 30 minutes to an hour, and a maximum of $15 USD for 24 hours. Or, choose the terminal garage, which offers hourly or daily rates. The daily lot has a 24-hour rate of $30 USD and is a long-term lot. You may also reserve a parking space ahead of time for a fee of $10 USD per space, per day.
The information and figures above are for reference only, and may not be current. Please visit each airport's website for up-to-date details.
Flights may be operated by Porter Airlines (Canada) Ltd or Porter Airlines Inc.
