Chicago The Loop

United States: a weekend to visit Chicago

To the point Discover Chicago! This American city is well worth a weekend visit. Here are our suggestions for activities you won't want to miss.

Our August 14, 2022 article has been updated with new activities and more money-saving tips.

Located in the United States, Chicago has something for everyone. Between cultural visits, restaurants, outings and parks, you’ll find that your weekend goes by too fast!

Chicago The River Chicago

Must-see tours in Chicago

Enjoy the city’s top tourist attractions with the Go City: Chicago All-Inclusive Pass.

See the city from above and visit the loop

Visit the Loop’ s bustling business district to take the pulse. Watch the train go by and climb to the top of the Willis Tower (formerly the Sears Tower) for its Skydeck. This skyscraper is an icon of the city and is one of the highest in the world.

The alternative to this observatory is the 360 Chicago Observation deck, which offers an equally superb view.

Chicago City View
Chicago The Loop

Take a boat ride in the evening

The walk along the Chicago River is enjoyable, and taking a cruise has become a must. We take the time to listen to the roar of the horns, the subways, to observe the architecture of its towers. It is a special atmosphere that we invite you to experience.

The alternative is to use the water cabs, which give you a similar, but stealthier view.

Bonus: take the evening stroll for a magnificent sunset over the skyscrapers!

We suggest this 90-minute night cruise on the river and lakefront or this 40-minute cruise on Lake Michigan.

Chicago Boat Taxi

Enjoy a typical Chicago pizza

Chicago is famous for its thick tomato pizza: Chicago style or deep dish pizza, baked in a high pan and generously topped with tomatoes and cheese.

Go for Lou Malnati’s or Gino’s East, which are among the best.

Chicago Pizza

Get your fill of attractions

Chicago’s Navy Pier is a fun walk that the whole family can enjoy. Every Wednesday at 9:30 pm and Saturday at 10:15 pm, a fireworks display takes place.

You can take a ride on the Ferris wheel, visit the Chicago Children’s museum, or sit down at one of the bars or restaurants. Or come to the Lobster Festival in September!

Chicago Children S Museum
Chicago Navy Pier

With the 360 Chicago view, on the 94th floor of the John Hancock Center over Lake Michigan and the city skyline, you can find a thrill ride, as if you were teetering off the edge of the building.

Cultivate your knowledge

There are many museums to see in Chicago. Here are just a few:

The architecture of the city is also superb. See skyscrapers, monuments like the Wrigley Building and art with “The Wings of Mexico” celebrating the city as a defender of immigrants and refugees.

The Chicago Architecture Center site offers exhibitions and events for all ages.

To make sure you don’t miss out on any of the city’s delights, book a guided architectural tour or a culinary, historical and architectural tour.

Chicago World's Largest Stained Glass Dome Tiffany Cultural Center Chicago
Chicago Claude Monet Art Institute Of Chicago
Chicago Mosaic In Tribute To French Explorer Jacques Marquette

Relax in the parks

The most famous is Millennium Park because it offers several contemporary art pieces, suchh as the Cloud Gate (the bean), a sculpture by Anish Kapoor. This giant bean will surprise and amuse you like everyone else with its reflections.

The Crown Fountain is another entertaining sculpture to see. It is composed of two giant blocks, from which water cascades out of the mouths of unknown faces.

Take a walk in Grant Park, the city’s green lung. Shows and festivals are also held here – watch for dates.

Finally, Lincoln Park is charming with its walks, multiple statues, and zoo. What’s more, admission is totally free.

Chicago The Bean
Chicago Park

Picnic on the beach or by the lake

Chicago’s beaches are great in summer! Some of them are supervised and well suited for swimming. We recommend Thorndale Beach for example.

The other option is Lake Michigan where you can relax and have a picnic. The lights are beautiful in the evening over the city.

Chicago Beaches

9 - Ride your bike around the city

In the off-season, you can take a bike ride along Lake Michigan, along the Chicago Riverwalk on the south side, or through the city’s various parks.

The bus is also a good alternative for discovering the city. We suggest this Chicago sightseeing bus tour with 11 different stops. You could also opt for a night tour by open-top bus.

Come out and have fun!

Theaters, musicals, festivals, jazz bars: there’s plenty on offer, so treat yourself to a lively evening. Watch for upcoming events on Eventbrite, TimeOut, or ChooseChicago!

Sit at Terrace 16 for a splendid view of the river on the 16th floor of the Trump International Hotel & Tower Chicago, the Radio Room for a lively evening or the Green Mill for its mythical venue, or try one of the best steak houses, Bodega Steak.

Chicago Theatre District

Hockey, baseball and basketball

If you want to see a Chicago Cubs baseball game, Wrigley Field is about 5 miles north of River North.

Chicago Bulls basketball and Chicago Blackhawks field hockey games are held at the United Center on the west side of the city.

Chicago - Save on your trip

Foreign currency transactions

If you’re planning a Chicago getaway, choose a credit card with no conversion fees. That’s 2. 5% savings per transaction!

Discover our tips in our guide to saving on foreign currency transactions.

Here are some cards with no conversion fees:

Getting there by plane

Flights to Chicago are frequent. You can use Flight Connections or Google Flight to help you find the best prices. It will be possible to use your Aeroplan miles.

You’ll need to use 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 maximize your points for travel to the U.S. with Aeroplan in this guide.

Not familiar with the Aeroplan program? In our beginner’s guide, we explain how to collect points easily.

The other option is to book through British Airways Executive Club. The program allows you to book flights on Oneworld Alliance airlines, includingAmerican Airlines. You can use Avios miles to pay for your flight.

However, availability is rare with Avios, especially for direct flights. You will need to use a tool like ExpertFlyer to find tickets with awards.

Chicago - Where to sleep

AirBnB and VRBO are particularly well represented in Chicago for renting between individuals. You can find your happiness by searching the site. However, you’ll need to plan well in advance to find attractive prices.

Marriott Bonvoy also offers an interesting rewards program. Here is our selection of hotels:

There are several ways to earn Marriott Bonvoy reward points. The easiest way is via credit card. American Express offers two credit cards linked to this loyalty program:

Each of these cards allows you to earn Marriott Bonvoy points directly through your daily spending, as well as through welcome offers.

Bottom Line

As you’ve seen, there are several options for planning a wonderful weekend in Chicago with the points. Use the Ulysses guides to plan your stay in Chicago:

Deux guides de voyage Ulysse sur la destination Chicago

We took the culinary walking tour with tastings. It was delicious! We were also recommended the gangsters and ghosts walking tour. There’s also a downtown tour with doughnut tasting, but you really need a sweet tooth to do it.

Don’t hesitate to share your addresses with our community!

Frequently Asked Questions

When is the best time to visit Chicago, Illinois, USA?

Spring and autumn are the best times to enjoy Chicago. Summers are hot and humid. Winters are dry and cold.

Where to go in Chicago with the family?

There’s plenty to keep your kids entertained in Chicago. The Museum of Ice Cream and the Chicago Children’s museum are must-sees. Navy Pier, with its Ferris wheel, is a fun ride for the whole family. Entrance to Lincoln Park Zoo is free.

What is it about Chicago that attracts tourists in particular?

Chicago’s architectural riches, numerous entertainment venues, upscale shopping, traditional Deep-dish pizza and nightlife in the North River district all appeal to tourists. The city center, nicknamed the Loop, is a must for art lovers. One of the best places to visit is the Art Institute of Chicago.

What to do on foot in Chicago

With its many attractions, downtown Chicago is the perfect place for a good walk. Millennium Park, a ten-hectare park, is located in the central part of the Loop.

Come to discuss that topic in our Facebook Group!
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Jean-Maximilien Voisine
Jean-Maximilien is an expert in Canada and France about Loyalty programs, Credit cards and Travel. He is the Founding President of Milesopedia.

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