Today we’re catching a 2 hour flight out of Toronto to Chicago for our very first winter weekend in The Windy City (spoiler: it really lived up to its nickname!)

STAY

For this trip, we booked a room at the W Chicago City Centre.

Chicago is considered the birthplace of modern architecture, and like so many of the businesses downtown, the W was converted from a historical building to a modern, stylish hotel that still pays tribute to its roots.

Make sure to stop into their on-site restaurant, IPO. We had an amazing breakfast!

PLAY

Chicago has a lot to offer when it comes to architecture, culture, and food. Just make sure to bundle up, because it can get very cold (and windy!) during the winter season.

MILLENNIUM PARK

Our first stop is a well known landmark in Chicago: Millennium Park, home to Cloud Gate, or at it’s more commonly known, The Bean.

THE ART INSTITUTE OF CHICAGO

For this weekend, we’ll be using the Chicago City Pass, which gets us access to all the major tourist attractions like The Art Institute of Chicago, one of the oldest and largest art museums in the United States.

360 CHICAGO

Our next stop is 360 Chicago in the John Hancock Building, which offers views of the city from 94 floors up.

CHICAGO ATHLETIC ASSOCIATION

Now it’s time to grab some food and drinks at the Chicago Athletic Association, an upscale hotel in a restored Gothic Style building. It’s got various spaces to explore with some amazing food and drinks, and you don’t need a be a guest of the hotel to check it out.

CHRISTKINDLMARKET

If you’re visiting during the holiday season, stop by Christkindlmarket in Daley Plaza. They’ve got a ton of vendors selling unique handcrafted items (perfect for gifting) and traditional snacks and beverages.

MUSEUM CAMPUS

Museum Campus is home to some of Chicago’s most notable attractions - and some great views.

NAVY PIER

The Ferris Wheel at Navy Pier offers some great views of the city and the shoreline.

EAT

Looking to indulge in some all-American dishes, Chicago style? Try the following!

PORTILLO’S

The Chicago dog is a staple here, loaded with a mix of tangy and spicy ingredients that are sure to get your tastebuds dancing. Portillo’s is an institution, so be prepared for a line!

CHICAGO-STYLE POPCORN

Sweet and salty is the flavour profile you can expect when sampling Chicago-style popcorn. It’s a mix of caramel and cheese, and while that might not sound like a natural combination, the two compliment each other well! You can get the good stuff at Garrett Popcorn Shops and Nuts on Clark is a favourite of ours!

GIORDANO’S OR LOU MALNATI’S?

When it comes to iconic dishes in Chicago, deep dish pizza takes the crown. But as far as where to get it? We’ll leave you to decide…

Oh, and if you’re feeling brave, don’t leave without doing a shot of malort!

We had such a fun first weekend in Chicago but I know there’s so much more to explore, so I’m looking forward to visiting again soon and checking out some of the many neighbourhoods and local experiences that Chicago has to offer.

If you’ve got some extra time, check out the best places to eat at Chicago O’Hare International Airport!

If you’ve got a favourite spot, let us know! See you next time… à la prochaine.