Fly non-stop from Toronto to Chicago and experience the city that’s always on the move no matter the season. It's that kind of city where you’ll find top notch cultural attractions, famous neighborhoods and architectural awes in just a few short strides from one another.
Even if your stay is just for a few days, make the most of your time in the Windy City with a few key points of interests you can’t miss. Take a bite out of Chicago’s own deep-dish pizza, wander through Millennium Park, stroll down the Magnificent Mile, catch a game at Wrigley Field, or visit Chicago’s long list of museums and art galleries. There are plenty of things to do in Chicago that will keep you entertained for days.
If it’s diversity you’re looking for, venture out to Chicago’s neighborhoods and experience a wide brush stroke of artist enclaves, stroller-friendly sanctums, tourist traps, massive-block stores and quaint boutique districts.
As you make your way through the eclectic mix of both tourists and friendly locals, you’ll be left with a jolt of contagious energy. You’ll look forward to another trip to Chicago from Toronto.
Wicker Park, a newly-rejuvenated neighbourhood near downtown Chicago, came to life in the mid-19th century, when the Rolling Mill steelworks opened and fascinated a wave of Irish labourers. Just a century and a half later, a melting pot of successive communities have called this neighbourhood their home.
The most recent demographic shift, sparked by a surplus of empty warehouses and affordable loft spaces, has been marked by a wave of artists, followed by white-collar professionals, flooding 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 most wanted neighbourhood has prevailed in the food industry, boasting some of the most sought after places to eat. Also known for its palate-pleasing nightcaps and breweries, Wicker Park has that award-winning dining experience that’ll satisfy the most insatiable appetite.
Looking for some fun things to do while in Wicker Park? Indulge in a little retail therapy. Along the northern division, on Milwaukee and Damen Avenue, you’ll find vintage shops and independently-owned fashion boutiques for the on-trend shoppers. If you’re more of a retail-chain shopper, there’s a healthy mix of big-name stores on that same block to satisfy.
Some think of Chicago as a meat-and-potatoes kind of town. But the neighbourhood of Logan Square is challenging that misperception.
Across its grid of sweeping, sycamore-lined boulevards, innovative new restaurants have been popping up everywhere, followed by gourmet coffee shops, galleries, newly inspired bars and fashion-forward stores.
“Local” still best describes the scene of this neighbourhood: ingredients are sourced locally at buzz-worthy restaurants, corner taps and craft breweries. Its galleries feature local artists of all ages while concerts and street fests feature startup bands. There’s no shortage of fun things to do in this great neighbourhood.
Centered on Logan Square itself, with its impressive Illinois Centennial Memorial Column, this is a neighbourhood with a solid scenery, resilient community and healthy ethnic diversity while enterprising newcomers are warmly welcomed.
The heart of this community is located in the actual “square” between Kedzie and Logan Boulevard where a roundabout meets at Milwaukee Avenue. The boulevards are surrounded by grassy, manicured medians and towering trees that are set on both sides. The neighbourhood has a name for these links, “Chicago’s Emerald Necklace,” an expansive system of interconnected parks, streetscapes, restored-Victorian homes and majestic churches.
Despite its appearance, Logan Square remains determinedly down to earth, and not, yet, another over-gentrified hipsterville. A visit to experience Logan Square’s many eateries and activities is well worth the trip from Toronto to Chicago.
Fly non-stop from Billy Bishop Toronto Airport (YTZ) to Chicago-Midway International Airport (MDW). Toronto to Chicago flight time is 1 hour and 50 minutes on average. The distance from Toronto to Chicago is around 715 km / 445 mi.
While onboard, sit back, relax, and enjoy our free drinks and snacks.
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.
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.
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.
Ubers are available for pick-up and drop-off at the airport.
The UP Express Train connects you between Union Station, Bloor Station, Weston Station and Pearson Airport. For ticket fares and schedules, visit upexpress.com
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.
Chicago Midway International Airport (MDW) is about 9 km / 6 mi from downtown Chicago.
The Go Airport Express shuttle bus provides service from the airport to downtown. The fare is $27 USD.
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 $20 USD per person. Car service is available.
Take the Chicago Transit Authority orange line from the Midway stop. The fare is $2.25 USD.