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United States: a weekend to visit Chicago

United States: a weekend to visit Chicago
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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!

United States: a weekend to visit Chicago - 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.

United States: a weekend to visit Chicago - Chicago City View
United States: a weekend to visit Chicago - 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.

United States: a weekend to visit Chicago - 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.

United States: a weekend to visit Chicago - 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!

United States: a weekend to visit Chicago - Chicago Children S Museum
United States: a weekend to visit Chicago - 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.

United States: a weekend to visit Chicago - Chicago World's Largest Stained Glass Dome Tiffany Cultural Center Chicago
United States: a weekend to visit Chicago - Chicago Claude Monet Art Institute Of Chicago
United States: a weekend to visit 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.

United States: a weekend to visit Chicago - Chicago The Bean
United States: a weekend to visit Chicago - 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.

United States: a weekend to visit Chicago - 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.

United States: a weekend to visit Chicago - 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.

Our credit card selection
Credit cardAnnual feeWelcome offer
Annual fee$120Welcome offer
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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:

United States: a weekend to visit Chicago - chicago-guides-ulysse

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!

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[vc_row][vc_column][vc_column_text el_class="checkmarks"]This metal credit card is the Best Aeroplan Business Credit Card in Canada. For a limited time, you can get, as a welcome bonus:
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With this Card you can earn:
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With this welcome offer for the American Express Aeroplan Business Reserve Card, you can earn up to 90,000 Aeroplan points:

  • Earn 65,000 Aeroplan points after making $10,500 in purchases in the first three months.
  • Earn an additional 25,000 Aeroplan points when you spend $3,500 in the 13th month.

With this Card, you earn 3X the points on purchases made directly with Air Canada and Air Canada Vacations. And 2X the points on hotels and car rentals. Everywhere else, you will earn 1.25X the points.

With this Card, you benefit from many Air Canada travel benefits such as access to Maple Leaf lounges in North America for you and one guest, priority check-in, priority boarding and priority baggage handling.

Enjoy your first checked bag free (up to 23kg/50lb) for up to 9 people travelling on the same reservation on Air Canada®* flights.

Like all American Express Canada Cards, there is no minimum income requirement.

Annual fee

Primary card$599
Additional card$199

Annual income required

Individual$0
Household$0

Conversion fees

2.5%

Earning rate

  • 3xAir Canada flights
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  • 1.25xAll spending

Value

1st Year Value$2,056
2nd Year Value$426

Card benefits

Concierge service24/7
Airport lounge access$400

Travel insurance

Travel medical (under 55)Up to $5,000,000 / 15 days
Travel medical (55-64)Up to $5,000,000 / 15 days
Trip CancellationUp to $1,500
Trip InterruptionUp to $1,500
Delayed BaggageUp to $1,000
Lost BaggageUp to $1,000
Flight DelayUp to $1,000
Hotel BurglaryUp to $1,000
Travel AccidentUp to $500,000

Purchase protection

Purchase ProtectionIncluded
Extended Warranty+1 years
Auto Rental Collision (primary)Up to $85,000 / 48 days

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.

Our featured card

Annual fee
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Our valuation
$350

Milesopedia first-year estimateFirst-year valueWelcome bonus$350Total$350Rewards on your spending are not included. The calculator that adds them from your own profile is on the card's page.

Welcome offer
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With this welcome offer for the Scotiabank Passport Visa Infinite +* Card +* CardMC, you’ll earn 25,000 welcome bonus Scene+ points after charging $2,000 in purchases to your account within the first three months.

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With the Scotiabank Passport Visa Infinite +* Card, you earn 3 points per $1 spent at Sobeys, IGA, Safeway, Foodland and participating Co-ops, and 2 points per $1 spent at other grocery stores, restaurants, eligible entertainment and eligible daily transit. You earn 1 point per $1 on all your other everyday purchases.

These points can be redeemed against any travel purchase at a rate of 1,000 points = $10 (flights, hotels, all-inclusives and even Airbnb), or as cash back with Scene+ at the same rate.

The Scotiabank Passport Visa Infinite +* Card also offers:

  • No fees for foreign currency transactions
  • 6 complimentary airport VIP lounge passes
  • Excellent insurance for your travels and purchases
  • Visa Infinite* Concierge Services

We have named this credit card the Best Credit Card with No Foreign Transaction Fees in 2024, 2025, and 2026.

Annual fee

Primary card$150
Additional card$50

Annual income required

Individual$60,000
Household$100,000

Conversion fees

0%

Earning rate

  • 2xGroceries
  • 2xRestaurants
  • 2xTransit
  • 2xEntertainment
  • 1xAll spending

Value

1st Year Value$650
2nd Year Value$397

Card benefits

Concierge service24/7
Airport lounge access$240

Travel insurance

Travel medical (under 55)Up to $1,000,000 / 25 days
Travel medical (55-64)Up to $1,000,000 / 25 days
Travel medical (65+)Up to $1,000,000 / 3 days
Trip CancellationUp to $1,500
Trip InterruptionUp to $2,500
Delayed BaggageUp to $1,000
Lost BaggageUp to $1,000
Flight DelayUp to $500
Hotel BurglaryUp to $1,000
Travel AccidentUp to $500,000

Purchase protection

Purchase ProtectionIncluded
Extended Warranty+1 years
Auto Rental CollisionUp to $65,000 / 48 days

Our editorial integrity

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