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 also, when it makes more sense to book with the travel points offered by your credit cards.
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
Book your flight with points
Using points should save you at least $300 on the cheapest flight found on the internet. And the points, whether Aeroplan or Avios or even AIR MILES, can be easily obtained with the various credit cards presented 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.
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 British Airways Executive Club. It allows you to book flights on Oneworld Alliance airlines and thus,American 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.
These Avios miles can easily be earned through welcome bonuses when you sign up for certain American Express, HSBC or RBC credit cards, or when you make purchases with these cards.
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:
- Club Quarters Hotel Wacker at Michigan for $297 CAD per night
- AC Hotel Chicago Downtown at $357 CAD per night
- or the Hotel Chicago Downtown – Autograph Collection available from $365 CAD.
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 :
- Courtyard Chicago Downtown/River North at CAD 284 per night or from 25,000 points per night.
- Fairfield Inn & Suites Chicago Downtown/Magnificent Mile: CAD 303 per night, available from 40,000 points per night.
- The Blackstone – Autograph Collection, from $393 or 40,000 points per night.
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.
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 BonvoyMD American ExpressMD* 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!
For a quirky Marriott hotel, opt for the St.Regis Chicago, which will open in March 2023. It is the third tallest skyscraper in Chicago and the tallest structure in the world designed by a woman.
Its undulating structure is connected with two other buildings, located at its sides. Room reservations will be available soon.
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 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.
2 - Take a boat ride in the evening
The walk along the Chicago River is enjoyable, and taking a cruise has become a must. You can take the time to listen to the roar of the horns, the subways, and to observe the architecture of its towers. It is a special atmosphere that we invite you to experience.
The alternative is to use the cab boats; you will get a similar but more stealthy view.
The little plus: take the walk in the evening for a magnificent sunset on the skyscrapers!
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.
Go for Lou Malnati’s or Gino’s East, which are among the best.
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!
With the 360 Chicago view on the 94th floor of the John Hancock Center of Lake Michigan and the city’s skyline, you can 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 Field Museum will introduce you to treasures about the history of human civilization.
- The Art Institute of Chicago is well known for all of its galleries with great works of art.
- The Museum of Science and Industry to visit for a flight simulation in … Boeing 747.
- The Chicago History Museum is the one to see if you want to know more about the city’s history.
- Finally, The Museum of Ice Cream is a colorful museum that will delight your children!
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.
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.
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. In addition, the entrance is totally free.
7 - Shop in the Magnificient Mile
A weekend out of the country is a good opportunity to look at what we have on offer in the 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 are nice 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.
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!
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.
Bonus: 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.
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:
Viator also offers excellent activities. We enjoyed taking a professionally guided walk. Booked on Viator, we did the Original Walking Food Experience in Chicago with Tastings.
With the very erudite and friendly Dave, we wandered the streets of River North to eat typical Chicago food:
- Chicago-style hot dog
- Deep-dish pizza
- Italian beef sandwich
It was delicious!
Dave also recommended the Chicago Gangsters and Ghosts tour. There’s also the donut tour, but you really have to have a sweet tooth to take it.
Finally, a must-do is to take the Chicago River Cruise to see the architecture. The guide on the boat was very interesting, with her anecdotes and jokes.
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