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In the United States, Chicago has something for everyone. Between cultural visits, restaurants, nightlife and parks, you will find your weekend goes by far too fast!
Enjoy the city’s main tourist attractions with the Go City: Chicago All-Inclusive Pass.
Visit the busy Loop business district to take the city’s pulse. Watch the train go by overhead and ride to the top of the Willis Tower (formerly the Sears Tower) for its Skydeck. This skyscraper is a city icon and one of the tallest in the world.
The alternative to that observation deck is the 360 Chicago Observation Deck, with a view every bit as superb.
The walk along the Chicago River is a real pleasure, and a cruise has become something of a must. You take the time to listen to the rumbling, the horns, the trains, and to study the architecture of the towers. It is a particular atmosphere, and one we invite you to feel for yourself.
The alternative is to take the water taxis: you get a similar glimpse, just a more fleeting one.
The little extra: take the trip in the evening for a magnificent sunset over the skyscrapers!
We suggest this 90-minute night cruise on the river and the lakefront or this 40-minute Lake Michigan cruise.
Chicago is known for its thick tomato pizza: Chicago-style, or deep dish pizza, baked in a deep pan and generously loaded with tomato and cheese.
Go for the one at Lou Malnati’s or Gino’s East, among the very best.
Chicago’s Navy Pier makes a pleasant stroll that the whole family will enjoy. Fireworks go off every Wednesday at 9:30 p.m. and Saturday at 10:15 p.m.
You can ride the Ferris wheel, visit the Chicago Children’s Museum, or sit down at one of the bars or restaurants. Or come during the lobster festival held in September!
With the view from 360 Chicago, on the 94th floor of the John Hancock Center over Lake Michigan and the city skyline, you will find a thrill ride that tips you out over the edge of the building.
Chicago has several museums worth seeing, among them:
The city’s architecture is superb too. Take in the skyscrapers, monuments such as the Wrigley Building, and art like “The Wings of Mexico”, which celebrates the city as a defender of immigrants and refugees.
The Chicago Architecture Center website lists exhibitions and events for all ages.
So as not to miss any of the city’s beauty, book a guided architecture walking tour or a food, history and architecture tour.
The best known is Millennium Park, home to several contemporary artworks, among them Cloud Gate (the bean), a sculpture by Anish Kapoor. This giant bean will surprise you, and you will have as much fun with its reflections as everyone else.
The Crown Fountain is another entertaining sculpture to see. It is made of two giant blocks, with water cascading from the mouths of unknown faces.
Take a walk in Grant Park, the green lung of the city. Shows and festivals are held there too, so keep an eye on the dates.
And Lincoln Park is a delight, with its walks, its many statues and its zoo. Entry is completely free, too.
Chicago’s beaches are a real pleasure in summer! Some are supervised and well suited to swimming. Thorndale Beach, for one, is worth a look.
The other option is Lake Michigan, where you can relax and have a picnic. The evening light over the city is beautiful.
Outside winter, you can cycle along Lake Michigan, along Chicago’s south-side riverwalk, or through the city’s various parks.
The bus is another good way to discover the city. We suggest this Chicago hop-on hop-off bus tour with 11 different stops. You could also choose this open-top double-decker night tour.
Theatres, musicals, festivals, jazz bars: the choice is wide, so treat yourself to a lively evening. Watch Eventbrite, TimeOut or ChooseChicago for upcoming events!
Sit down at Terrace 16 for a splendid river view from the 16th floor of the Trump International Hotel & Tower Chicago, the Radio Room for a lively evening or the Green Mill for its legendary setting, or try one of the best steakhouses, Bodega Steak.
To catch a baseball game with the Chicago Cubs, Wrigley Field is about 8 kilometres north of River North.
Chicago Bulls basketball games and Chicago Blackhawks hockey games are at the United Center, west of the city.
If you are planning a getaway to Chicago, choose a credit card with no foreign transaction fees. That is a 2.5% saving on every transaction!
Find our tips in our guide to saving on foreign currency transactions.
Here are some cards with no foreign transaction fees:
Flights to Chicago are frequent. You can use Flight Connections or Google Flights to help you find the best fares. You will be able to use your Aeroplan points.
You will need at least 10,000 Aeroplan points, departing from Montreal, for a one-way economy flight to Chicago airport, according to Air Canada’s points predictor. Find out how to make the most of your points to travel to the United States with Aeroplan in this guide.
Not familiar with the Aeroplan program? Our beginner’s guide explains how to earn points easily.
The other option is to book through The British Airways Club. The program lets you book flights on Oneworld alliance carriers, and so on American Airlines. You can therefore use Avios to pay for your flight.
Availability with Avios is scarce, though, above all on direct flights. You will need a tool such as ExpertFlyer to find award tickets.
Airbnb and VRBO are particularly well represented in Chicago for private rentals. You will find what you are after by searching the site. You will have to book well ahead to get attractive prices, though.
It is also worth looking at Marriott Bonvoy, whose program offers attractive rewards. Here is our selection of hotels:
There are several ways to earn Marriott Bonvoy reward points. The simplest is through credit cards. American Express offers two credit cards tied to this loyalty program:
Each of these cards earns Marriott Bonvoy points directly through your everyday spending, and through the welcome offers as well.
As you have seen, there are several ways to organise a magnificent weekend in Chicago with points. Draw on the Ulysse guides to plan your stay in Chicago:
We did the walking food tour with tastings. It was delicious! We were also recommended the gangsters and ghosts guided walking tour. There is also the downtown donut tour with tastings, but you really need a sweet tooth for that one.
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