Chicago Travel

The PerfectCouple Guide to CHICAGO

For Victoria day week-end back in May, my girlfriend and I visited Chicago and we immediately fall in love with the city.

On a Friday morning, we took off from Montreal really early in the morning and got to O’Hare airport about 8am. to avoid the rush hour traffic, we decided to take the train all the way to downtown which was really convenient since we were traveling only with a carry on. This was our first time in this city and we absolutely loved the experience.

Chicago is legendary for its architecture and the best way to discover the city’s skyline is by taking Chicago’s First Lady Boat Tours. During the 90 min river tour, the guides do a hell of a job explaining the history, the authors and some of the stories about the different buildings and bridges around the city. Definitely one of my favorite activities of this trip and the best way to see the city of Chicago.

The windy city  has many drawbridges; the most of any city in North America, in a mere two miles, there are eighteen movable bridges.  If you love architecture you’ll get your hands full in Chicago.

On the other hand, some of the things that we both loved about the city is the variety of restaurants and the quality of the food, since in Montreal we have really good restaurants, sometimes we are disappointed when we go abroad, but this wasn’t the case.

4 day Guide to Chicago4 day Guide to Chicago4 day Guide to Chicago 4 day Guide to Chicago 4 day Guide to Chicago 4 day Guide to Chicago4 day Guide to Chicago 4 day Guide to Chicago4 day Guide to Chicago4 day Guide to Chicago

As a first time visit to the windy city I recommend staying at least three full days to explore. If you are planning on visiting Chicago, here are some of the perfect couple suggestions

Where to stay

4 day Guide to ChicagoFelix Hotel– It’s a great contemporary space, well located and  has everything you need when visiting a big city such as Chicago.


4 day Guide to Chicago4 day Guide to ChicagoLake Front Trail– get your early morning work out done at this trail, whether you walk, run, or bike, the trail offers one of the best views of Lake Michigan and also the city.

4 day Guide to ChicagoChicago 360 Observation Deck-Located on the 94th floor of the John Hancock center, Chicago 360 Observation deck offers breathtaking views of the city and also the lake, The building is located at 875 N. Michigan Avenue. If you want to get the best pictures, I recommend you to get there early  to avoid the crowds and line-ups.

4 day Guide to Chicago

Cloud Gate-One of the most famous landmarks in Chicago is “the Bean”,  this beautiful sculpture is a must do when visiting Chicago and is located at Millennium Park.

4 day Guide to ChicagoNavy Pier–  A great new contemporary urban space, where you’ll find restaurants, a huge wheel of fortune,  patios, stores, gorgeous views of the city and lake Michigan.

4 day Guide to Chicago 4 day Guide to Chicago 4 day Guide to ChicagoFulton Market– The unique mix of  industrial past and urban present makes Fulton Market one of the coolest places in Chicago. This place is really similar to the Meatpacking district nieghborhood in New York. What makes this place really unique is that all warehouses and old bricked buildings were turned into trendy restaurants, coffee shops, condos and art galleries. The vibe of this place is amazing, the restaurants were packed and there was people everywhere.                 


Michigan Ave-From tech stores to high end and upscale brands are all situated here.

Oak St– One of the most gorgeous streets in Chicago,  you’ll find high end boutiques, international couture houses and restaurants. This is the Chicago luxury shopping destination.

Sports & Activities

Ball Game– Unfortunately the Cubs were away during this week-end so we did not have the opportunity to visit Wrigley Stadium. But if you happen to visit Chicago and it’s baseball season, make sure you don’t miss this opportunity. Another option, if you are visiting Chicago during the fall would be to visit the Soldier field, home of the Chicago Bears.


4 day Guide to Chicago4 day Guide to ChicagoLittle Goat Diner-Delicious food in the heart of Fulton Market neighborhood, this place takes no reservations, so make sure you get there early.


4 day Guide to Chicago4 day Guide to Chicago4 day Guide to ChicagoCindy’s rooftop-Located on the rooftop of Chicago’s athletic hotel, Cindy’s rooftop offers the best cocktails in the city and I mean it. The place is stunning, the decor and the view is breathtaking.

4 day Guide to ChicagoCity Winery– Grab a local glass of wine, enjoy the view of the river and watch the boats go around.


Coffee Shops & Juice Bars

4 day Guide to Chicago4 day Guide to ChicagoStudio Three-Get your work out done before heading to discover the city, grab a delicious acai bowl and/or a green juice and start your day right. I wish we had these fitness boutiques concepts here in Montreal.

Café Umbria– cool little coffee shop located downtown core, best coffee I’ve had in Chicago.

Cafe Umbria



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