Fly from Montréal to Chicago, to take in the air of the Windy City.
From the top of the Willis Tower to the bottom of its deep dish pizza, Chicago offers plenty to see and explore. This Midwestern American city takes its architecture and cuisine seriously but still knows how to have fun.
If you’re looking for fun things to do in Chicago, start on the shores of Lake Michigan. The Navy Pier has 50 acres of museums, amusement rides, and movie theatres, making it one of Chicago’s most entertaining attractions.
Stay close to the water, with a walk along Chicago’s Lakefront Trail. You don’t have to run or cycle all 18 miles of the path, but you’ll certainly enjoy the views along the way. While you’re admiring the city, you’ll notice that Chicago is dotted with amazing architecture everywhere. In Millennium Park, the Jay Pritzker Pavilion frames a futuristic venue for outdoor concerts.
To see more of Chicago’s best architecture, look down almost any street. From its trident topped dome to its fossil covered floors, the Shedd Aquarium is a building worthy of Neptune himself. The Tiffany glass dome of the Chicago Cultural Centre is similarly aquatic. With glass cut in the shape of fish scales, this impressive dome shines a light on Chicago’s public art events.
Dating back to 1914, Wrigley Field is one of the most beloved structures in Chicago. But this baseball field isn’t the only game in town. Choose your side in a long-standing rivalry between the city’s two MLB teams. Whether you see the Chicago Cubs at Wrigley Field, or the Chicago White Sox at US Cellular Field, a day spent watching America’s pastime is a home run for all ages.
Another longstanding Chicago rivalry is between the city’s pizza places. No trip from Montréal to Chicago would be complete without indulging in a slice of deep dish. With competition as fiery as the ovens, everyone wins.
On your trip from Montréal to Chicago, stop for a visit to delicious Logan Square and enjoy a midwestern culinary adventure.
Locally sourced ingredients can be found on the area’s buzz-worthy menus and in its hip and hoppy craft brews. Logan Square’s restaurants range from farm-to-table health food, to tooth-achingly sweet bakeries. With options for every taste, this neighbourhood is simmering with some of Chicago’s best eateries.
Once you’ve eaten your fill, walk off your wood-fired pizza in one of Logan Square’s art galleries. Work from local artists line the walls of these spaces, adding a community feeling to the arts scene.
See art on a larger scale at the Congress Theatre and Concord Music Hall. These two music halls along Milwaukee Avenue stage bigger-name acts. If you’re looking for the local talent, Logan Square’s street festivals are humming with the sounds of underground bands.
As a park and part-time performance venue, the Bloomingdale Trail and Park is one of the most innovative green spaces in Logan Square. Known as the 606, this converted rail line features permanent and temporary art exhibitions along its 3-mile length.
After you’ve taken the Bloomingdale Trail, head south to nearby Humboldt Park to round out your trip from Montréal to Chicago. This neighbourhood has Chicago’s best Puerto Rican food, speciality shops, and, of course, the eponymous Humboldt Park.
Whether you go from Montréal to Chicago for business or leisure, The Loop is a must-see stop.
Stay in the loop of Chicago’s architecture scene with a visit to this neighbourhood. As the city’s business centre, even the busiest traveller will have time to see some of the best architecture in Chicago. Formerly called the Sears Tower, and once the tallest building in the world, the Willis Tower is a staple of the Chicago skyline. On the glass bottomed balconies of this 108 story building, you can get a stomach-dropping sense of this building’s scale.
While it may not be tall enough to be seen in the city’s skyline, the Rookery Building is a historic landmark. Built after the ravages of the Chicago Fire, the Rookery was completed in 1888. It wasn’t until 1905 that one of its most famous features, the lobby designed by Frank Lloyd Wright, was added. With tours open to the public, you won’t need to take a meeting here to look around the Rookery.
After seeing some of the world’s most well-known paintings in the Art Institute of Chicago, step outside to find more works of art. Walk by Cloud Gate, better known as “The Bean”, to enter Grant Park. From the Frank Gehry-designed Jay Pritzker Pavilion in Millennium Park to the statuary in the Formal Garden, Grant Park’s different areas each have their own artistic feel.
If one of Grant Park’s outdoor concerts gets rained out, take refuge in the Chicago Symphony Orchestra building. Like Montréal, Chicago’s jazz scene is legendary. Since 1947, Jazz Showcase has been improvising its way into the hearts of locals and visitors alike. Top off your day in The Loop with an evening in this intimate venue, listening to some of Chicago’s best jazz.
Fly from Montréal-Pierre Elliott Trudeau International Airport (YUL) to Chicago Midway International Airport (MDW), with a quick connection in Toronto. Montréal to Chicago flight time is 3 hours on average. Connection times vary. The distance from Montréal to Chicago is around 1205 km / 750 mi.
Enjoy complimentary drinks and snacks along the way.