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Chicago The Loop

Visit Chicago with points and miles

To the point Visiting Chicago for a weekend is doable with points and miles! Take a look at our tips for lowering the cost of your stay and the activities to do there.

With all our tips, a weekend in Chicago is easily achievable for less than $250.

Let’s take a closer look at how you can make the most of your hotel points & airline miles and when it makes more sense to book with your credit card travel points.

Getting to Chicago by plane

Several airlines offer direct flights to Chicago or with a stopover in:

  • Toronto: Air Canada, United Airlines, Porter
  • Washington / New-York : American Airlines
  • Chicago / Philadelphia / Charlotte / Detroit : Delta
Chicago The River Chicago
Chicago The River Chicago

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.

Book your flight with points

Using miles should save you at least $300 on the cheapest flight found on the internet. And the miles, whether Aeroplan or Avios or even AIR MILES, can be easily obtained with the various credit cards shown below.

Looking around, we saw flights for $358 roundtrip on Air Canada between Montreal and Chicago on direct flights over the Thanksgiving weekend. Comparatively, in points, this ticket was 14,000 Aeroplan points and $85.

Chicago Argent
Chicago Aeroplan

If we calculate the valuation of a point, we arrive at this result:

(358 $ – 82 $) ÷ 14 000 x 100 = 2 ¢

Milesopedia gives a valuation of 2¢ per Aeroplan point, so we are exactly on the desired value!

The other option is to book through the British Airways Executive Club, which allows you to book flights on Oneworld Alliance airlines. In this case, it isAmerican Airlines. You can use Avios miles to pay for your flight. However, availability is rare with Avios, especially for direct flights; you’ll need to use a tool like ExpertFlyer to find award tickets.

These Avios miles can quickly be earned through welcome bonuses when you apply for particular American Express, HSBC or RBC credit cards or when you make purchases with these cards.

Chicago Avios

You will be able to redeem your Membership Rewards American Express (1:1 transfer rate), HSBC Rewards (2.5:1), and RBC (1:1) points for Avios miles: transfer during the bonus conversion periods!

The flight cost can even be reduced to $0 by applying your Scene+ points (10,000 points = $100) if you have an American Express Gold from Scotiabank, for example.

In this case, the bonus points on this card are more than enough to get you a free flight!

Hotel nights in Chicago

Let’s look at the options available to you in Chicago. Many hotels are available by searching for hotels via Booking. For example:

Here are some other options to consider to find a better price.

The rental option

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 to find reasonable prices, ranging from CAD 200 to $350 per night.

If you have never used AirBnB before and go through this link, you will get a discount on your next booking.

We recommend you to use one of these 3 hosting solutions if you are several.

The rental causingized with different cards offering travelhaveints:

A hotel with the points

You might want to look into Marriott Bonvoy, which offers a program with some exciting rewards. We advise you to book directly on the Marriott website for the best prices. Some examples of rates found :

If you prefer to pay, the former would be the best choice. But if you use your points, we advise you to book the higher category hotel to get the best value for your points.

The number of points varies according to the period and the category of hotel chosen, be flexible and book in advance to have the chance to get the best rates.

Blackstone Chicago Autograph Collection

If you don’t have enough points, you could take the first night at a hotel near the Airport like the Aloft Chicago O’Hare from 17,000 points (CAD 202 per night) if you arrive on Friday evening. You will reduce the number of points needed for your stay or at the

By combining this with the centrally located Courtyard, your 3-night stay in Chicago would be 71,000 Marriott Bonvoy points. These points could be earned through the Marriott Bonvoy® American Express®* Card (75,000 Marriott Bonvoy points) with an annual membership fee of only $120.

If we do the math, your stay in Chicago would cost about $760 for three nights. With $120 in contributions and the welcome bonus, you save over $600!

Chicago Best Western

Finally, if you prefer to look at Best Western hotels in Chicago, the Best Western Grant Park Hotel starts at $290 and is very well located for sightseeing.

Must-see tours in Chicago

Chicago has something for everyone. Between cultural visits, restaurants, outings, and parks, you will find that your weekend goes by too fast!

1 - See the city from above and visit the loop

Visit the Loop’s bustling business district to feel 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 tallest in the world.

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

Chicago City View
Chicago City View
Chicago The Loop
Chicago The Loop

2 - 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 humming, honking trains of the city, to observe the architecture of its towers: a unique atmosphere that we invite you to feel.

The alternative is to use the cab boats; you will get a similar but more stealthy view.

The little plus: take a walk in the evening for a magnificent sunset on the skyscrapers!

Chicago Boat Taxi
Chicago Boat Taxi

3 - Enjoy a typical Chicago pizza

Chicago is known for its particular tomato pizza: the Chicago style or deep dish pizza, cooked in a high pan and generously topped with tomatoes and cheese.

Chicago Pizza
Chicago Pizza

4 - Get your fill of attractions

Chicago’s Navy Pier is a fun walk that the whole family can enjoy. A fireworks display is held every Wednesday at 9:30 PM and Saturday at 10:15 PM.

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 Children S Museum
Chicago Navy Pier
Chicago Navy Pier

In addition to the 360 Chicago view on the 94th floor of the John Hancock Center of Lake Michigan and the city’s skyline, you’ll find a thrill ride, as if you were tipping off the edge of the building.

5 - Cultivate your knowledge

There are several museums to see in Chicago, here are some of them:

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

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

6 - 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 you, and you will love it as much as anyone.

Another entertaining sculpture is the Crown Fountain, composed of two giant blocks from which water cascades out of the mouths of unknown faces.

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

Finally, Lincoln Park is charming with its walks, multiple statues, and zoo.

Chicago The Bean
Chicago The Bean
Chicago Park
Chicago Park

7 - Shop in the Magnificient Mile

A weekend out of the country is an excellent opportunity to see what we offer in American stores! Do window shopping and use the right credit card like the HSBC World Elite® Mastercard® card to avoid conversion fees.

8 - Picnic on the beach or by the lake

Chicago’s beaches may not be the most beautiful in the U.S., but they’re excellent in the summertime! 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
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.

10 - Go out and have fun!

Theatres, musicals, festivals, jazz bars: the offer is excellent, so treat yourself to a lively evening. Watch for upcoming events on Eventbrite, TimeOut, or ChooseChicago!

Sit at Terrace 16 for a great 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 legendary venue, or try one of the best steakhouses, Bodega Steak.

Chicago Theatre District
Chicago Theatre District


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:

Chicago Guides Ulysses
Chicago Guides Ulysses

Viator also offers excellent activities:

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

Come to discuss that topic in our Facebook Group!

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