What to Do in Chicago

Getting there from Ontario: Chicago sits roughly 8 hours from Toronto by car via Highway 401 and Interstate 94 through Detroit — a manageable drive for a long weekend. Direct flights from Pearson run under 90 minutes, while VIA Rail connections via Amtrak's Maple Leaf offer a scenic alternative. US border crossing at Windsor–Detroit or Niagara Falls is straightforward for Canadian citizens with a valid passport.

There is a reason Chicago has held its place as one of North America's great cities for well over a century. It rebuilt itself from ash after the Great Fire of 1871 and in doing so invented modern architecture, gave the world jazz and blues in forms all its own, and became a food city whose reputation stretches from deep-dish pizza to Michelin-starred tasting menus. For travelers from Ontario, it offers everything a major American destination should — genuine world-class culture, outstanding museums, a walkable lakefront, and a distinct character that feels nothing like New York and nothing like Los Angeles. The Windy City earns its nickname not just from its weather but from the ambition of the people who built it.

Whether you are crossing the border for a first visit or returning after years away, Chicago consistently rewards the curious traveler. The following guide covers the experiences that define the city, with practical booking information for each.

Chicago Architectural Sightseeing Cruise

No introduction to Chicago is more fitting than a cruise along the Chicago River as it threads through the downtown canyon of towers. The city's architectural legacy is genuinely unmatched in North America — the Loop and its surroundings contain more landmark skyscrapers per block than anywhere else on the continent, and viewing them from water level grants a perspective that no street-level walk can replicate. The river reflects the glass and steel of buildings by Louis Sullivan, Mies van der Rohe, and Bertrand Goldberg, each generation of construction layered atop the last in a living textbook of modern design.

The 45-minute architectural cruise is a particularly well-paced introduction, long enough to absorb the key landmarks — the Marina City corncobs, the Tribune Tower with its gothic stonework, the steel curves of 333 Wacker Drive catching the morning light — without becoming overwhelming. Guides are typically well-informed and enthusiastic, and the boats are open-air or enclosed depending on the season. It is one of the few tourist experiences in any city that consistently earns its reputation with repeat visitors. Families will find it genuinely engaging for children old enough to appreciate scale.

The Field Museum of Natural History

The Field Museum sits at the southern end of Grant Park, flanked by Lake Michigan and the city's skyline, in a neoclassical building grand enough to warrant a visit before you have even stepped inside. Founded in 1893 for the World's Columbian Exposition, the museum holds over 40 million specimens and artifacts spanning every continent and every era of natural and human history. It is, in the truest sense, a collection assembled when the ambition of American institutions was effectively unlimited.

The permanent exhibitions cover ancient Egypt with genuine mummies and reconstructed tombs, Indigenous peoples of North America with collections assembled over a century of fieldwork, and natural history ranging from gemstones to taxidermied African wildlife displayed in painstakingly recreated dioramas. Sue the T. rex, one of the largest and most complete Tyrannosaurus skeletons ever discovered, stands in the main hall and reliably stops visitors cold. Rotating special exhibitions add fresh reasons to return even for those who have visited before.

For travelers from Ontario with children, the Field Museum competes comfortably with the Royal Ontario Museum in scope while offering a distinctly different curatorial perspective — more natural history, deeper on the Americas. Budget at minimum three hours; a full day is not excessive.

360 Chicago Observation Deck

The John Hancock Center — rebranded 875 North Michigan but still called the Hancock by every Chicagoan — stands on the Magnificent Mile with a directness that the Willis Tower, buried deeper in the Loop, cannot match. Its observation deck on the 94th floor places you squarely above Michigan Avenue with unobstructed sight lines north along the lakeshore and south over the full sweep of the downtown skyline. On a clear day, the view extends across Lake Michigan toward Michigan and Indiana; on summer evenings, the light on the water is extraordinary.

The 360 Chicago experience includes TILT, an enclosed viewing platform that slowly tilts visitors outward at a 30-degree angle over the street below — a feature that divides opinion sharply but is particularly memorable for those who can handle the sensation. The deck itself is worth the visit regardless, and queues tend to be shorter than at the Willis Tower, making it a more relaxed option for families or those without a high tolerance for crowds.

Navy Pier Centennial Wheel

Navy Pier stretches 1,000 metres into Lake Michigan from the Near North Side, a former naval training station transformed into Chicago's most-visited attraction. The Centennial Wheel — a 61-metre Ferris wheel completed in 2016 to replace the original — anchors the eastern end of the pier and provides a slow, sweeping panorama of the city's lakefront skyline that no ground-level vantage point can rival. The enclosed gondolas are climate-controlled, making this a viable experience across seasons.

The pier itself is worth an hour of wandering beyond the wheel: outdoor beer gardens in summer, a winter WinterFest market in December, the Chicago Shakespeare Theater housed in a purpose-built facility, and a selection of restaurants ranging from casual to credible. It is an unabashedly touristic space, but Chicago does not apologize for it, and the views from the water's edge toward downtown — the skyline rising above the lakefront parks — are among the best the city offers at ground level.

Flyover Chicago at Navy Pier

Flyover Chicago is the city's most technologically immersive attraction — a motion-simulation flight experience that suspends riders on a hanging seat system in front of a hemispheric screen, then takes them on a cinematic journey over the city's landmarks at speed. The production is genuinely impressive: high-resolution footage, synchronized wind, mist, and scent effects, and a flight path that covers everything from the river and the Loop to the lakeshore parks and beyond. It is closer to a theme-park ride than a sightseeing experience, but executed at a quality level that justifies the distinction.

For first-time visitors who want to understand Chicago's geography before exploring on foot, Flyover provides an orienting overview that no map or rooftop deck can replicate. The experience runs approximately eight minutes and departs in groups, so queues move efficiently. It sits at Navy Pier, making it easy to combine with the Centennial Wheel for a full afternoon on the lakefront.

Planning Your Chicago Weekend from Ontario

Two full days in Chicago cover the highlights at a comfortable pace; three days allow genuine exploration of neighborhoods beyond the tourist core — Lincoln Park, Wicker Park, Pilsen, Hyde Park. The city's transit system (the L train) is efficient and inexpensive, and most of the attractions above cluster along the lakefront between Navy Pier and Museum Campus, making them easy to combine without a car. Accommodation along the Magnificent Mile or in River North puts everything within walking distance.

For the return drive to Ontario, the Ambassador Bridge crossing at Windsor remains the busiest but often the fastest route; Blue Water Bridge at Sarnia is a reliable alternative when Detroit is congested. Arrive at the border with receipts for anything purchased — US duty-free allowances apply for stays over 48 hours. Chicago is, by any measure, one of the great American cities, and for travelers from Ontario it remains among the most accessible and most rewarding destinations south of the border.