Chicago – The Loop, Magnificent Mile & Lake Michigan

On our second day in Chicago we woke up to a very grim and cold day. Such a change from the 40+ degree heat we’ve been experiencing over the past few weeks!

As we had planned to visit the Chicago Art Museum anyway, we thought today would be perfect to do so to escape the bad weather.

The Art Institute of Chicago is one of the best art museums in the world. It houses thousands of pieces from all around the world in its massive halls.

Being a big fan of Impressionism myself, it was such a treat as they have a huge Impressionist wing, including works from Monet, Cézanne, Renoir and more.

They also had a fabulous exhibition on Manet’s latest artworks before his death, including ‘Spring’, one of his biggest and most well known pieces. We had an amazing time there!

After our culture fix we made our way to Millenium Park to check out the numerous sculptures dotted around. Chicago is such a beautiful city, with old architecture seemlessly mixed in amongst modern sky scrapers.

After checking out the park, we made our way to the Nutella flagship store for a snack (because obviously), before strolling around the streets in downtown.

The next morning we decided to dedicate the day to the river walk and the Magnificent Mile. The Chicago River flows next to the Loop, and you can enjoy a beautiful walk along the riverside.

We walked all the way from the Union Train Station to the Trump tower and the bottom of the Magnificent Mile. We then walked the magnificent mile; this stretch of road is home to numerous fashion and high end jewelry stores, again mixing old buildings with new skyscrapers.

We then headed towards Gold Coast, the very fancy neighborhood filled with luxurious town houses and nice restaurants. We specifically headed there to check out the original Playboy Mansion, previously owned by Hugh Heffner back in the days and where he initially started his magazine. The area is gorgeous and very near the lake.

We then walked towards the Loop to check out the different second hand jewelry shops on Wabash Street, before going for a drink at Cerise, the bar at the top of the Virgin hotel with a beautiful view over the city.

We initially went to Cindy’s, another rooftop in front of Millenium Park, but we both agreed the view wasn’t mind blowing and with no chairs to rest our tired legs we preferred to check out Cerise instead. Glad we did.

On our forth and final day, we planned to rent bikes and cycle the lake front.

The path goes all the way from north on Foster beach down south to Hyde Park. The total length of the path is 18 miles. It is very flat, easy to navigate with sign posts everywhere, and has got gorgeous views over the city. It’s also been newly renovated so the path is great to cycle on.

We found a good 50% off deal online and booked our bikes from Bike & Roll for $43 (for both bikes for the day, pretty good price).

We could have gone with the Divvy bikes for a slightly cheaper price (phone app city rental bikes) but they seemed very bulky and uncomfortable for a full day of cycling. You also have to dock them every 3 hours, seemed annoying.

We decided to head north for the day and stop first for a stroll up the Navy Pier. It was very pretty, with a big ferris wheel and a long pier providing gorgeous city views.

We then continued cycling up towards Oak Street beach and left our bikes there to enjoy a nice lunch at Lou Malnati’s Pizzeria, one of the other big players in the deep dish pizza (we had to compare).

Our verdict: Giordano’s wins.

After lunch we continued to make our way north up to the end of the trail, over 8 miles away before circling back the way we came from, this time with the city in sight at all times.

We paddled in the water but the lake was freezing cold, so we didn’t bother trying to get in.

We had an amazing day and overall really enjoyable time in Chicago.

Despite the crazy shooting rate (there were 61 shootings over the 4 days we were there!) we didn’t see or hear anything and felt very safe everywhere.

Tomorrow we’re finally making our way to New York (we’re super excited about it)!


  • If you’re going to try just one pizzeria to eat proper deep-dish, go with Giordano’s. They have a few restaurants around the cities you can check out.
  • If you like art of any kind, the Art Institute of Chicago is a must do. You can get combined tickets with the Willis Tower observatory tickets and save $2 (and time so you don’t have to queue twice). You can also buy them online here.
  • Cycling is a great way to see the city. Bike and Roll’s bikes were great, in good condition and for a good price with their discount code. You can find them here.

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