CityGuide: Chicago

Things to do in Chicago: As Voted by our Aeroplan Members

Chicago’s architecture is always a reason to visit. PHOTOGRAPHY ANGUS MCRITCHIE

Updated October 2014

Chicago is a city that begs to be explored on foot, with detailed brickwork and artful signage, and new discoveries at every corner. Between Chicago’s famous central attractions (Millennium Park, the Loop) and its historic suburbs is a city still roaring with energy, one you can enjoy in a weekend or spend a lifetime getting to know. The towering skyscrapers may seem daunting, but look closer and they’ll reveal as much character and warmth as the city itself. A morning stroll through Magnificent Mile — the ritzy shopping district just steps north of Chicago’s downtown core (the Loop, in local parlance) — carries the smell of roasting cocoa beans from the Blommer Chocolate factory on the breeze. In this town, the surprising is always lurking just below the familiar.

Aeroplan Members are pretty seasoned travelers.  We’ve asked them for their opinion when it comes to their top picks for where to stay, where to eat, and what to do.  We’ve tallied all their votes and have been able to identify the best of Chicago, as voted by our Aeroplan Members.

Where to Stay
Waldorf Astoria Chicago

Pictured Above: Waldorf Astoria Chicago

There are so many great options when it comes to places to stay in the windy city.  The city is filled with great hotels and we know it can be sometimes hard to choose the best place.

We’ve asked our Aeroplan Members which Aeroplan Partner Hotels they prefer to stay with when travelling to Chicago and they have made their voices heard. They have identified the top 10 hotels in Chicago.  The clear winner was the Waldor Astoria Chicago which is Chicago’s premier luxury hotel in the downtown area. The rooms are spacious and have everything you ever wanted in a “home away from home.”  It truly is luxury meets every day indulgence and we’re not surprised to see this Aeroplan Partner Hotel made the top of the list.

Looking for a more trendy spot? The W Chicago City Center came in a close second on the top 10 list. The location is fantastic, the building is gorgeous and the service, from the staff and the concierge are world class. Like so many W hotels, they have a great bar called Plateau Bar, the perfect place to unwind with one of their many signature cocktails.

Top 10 Places to Stay in Chicago as Voted by our Aeroplan Members:

Earn miles at any of these hotels.  

Where to Dine
Joes Seafood Chicago

Foodies love Chicago. From elite practitioners of molecular gastronomy to the gut-busting deep-dish pizzas, the city is crawling with fine yet funky eateries.  There is a lot to take in and it’s hard to try just one place.

We’ve asked our Aeroplan Members which restaurant they think is the best place to eat while in Chicago. Our members voted Joe’s Seafood  Prime Steak & Stone Crab as the best places to eat in Chicago.
Joe’s Seafood, Prime Steak & Stone Crab is known for its crab bisque and chopped seafood salad, but we highly recommend the large stone crabs. Looking to satisfy your sweet tooth? Try the key lime pie (we’ve heard it’s better than Miami’s!)

Want to see the full list? 

Here are the Top 5 Places to Eat in Chicago as Voted by our Aeroplan Members

What to Do

chicagoA trip to Chicago isn’t complete if you haven’t spent some time in Millennium Park, located off of Michigan Avenue between East Randolph St and East Monroe Street, the park is a perfect place to watch the city go by or pose with “the bean.” There is more to the park than just the world famous bean, there is state-of-the-art architecture, landscapes and many free cultural activities include concerts and tours. Check out the city of Chicago’s monthly schedule to see what you can take advantage of during your next trip.

Here are the top 5 things to do while in Chicago as voted by our Aeroplan Members

  • Visit Millennium Park
  • Spend some time at the Art Institute of Chicago
  • Watch a game at Wrigley Field
  • Visit the Holy Name Cathedral
  • Check out the Chicago Cultural Center

Let us know if our Aeroplan Members got this list right. What is your “must do” in Chicago?

5 Responses to “CityGuide: Chicago”

  1. Sheila Dropkin March 20, 2015 at 12:00 pm #

    This information is 2 years old. Is there an update? I understand that there is (or was) an architectural tour given by boat on the lake (is it Lake Michigan?) – is this still available in the summer?

    • Aeroplan April 10, 2015 at 3:07 pm #

      Hi Sheila,

      Note that this was a list compiled from member votes. We do update our City Guides around certain events or when information has become outdated. As for the tour of Lake Michigan – it seems there are some tours available. If you have any ideas or suggestions that you would like to add for members traveling to Chicago, please feel free to add them 🙂

      Thank you!

  2. L. Bruce August 12, 2013 at 3:59 pm #

    This posting is dated May 2010. Are you planning an up-date ?

    • Aeroplan September 23, 2013 at 11:16 am #

      Yes we are working on updating these guides right now. We hope to have these updated shortly!
      Thank you for your feedback!

  3. Daniel Clendinneng July 19, 2013 at 1:47 pm #

    Thank you for the info on Chicago.
    I think it is a great marketing idea/customer service to send your Aeroplan customers the City Guide of the destination they just booked.
    I will definitely check out some of the places you listed in the blog.
    Best regards,
    Danny Clendinneng