Weekend in Chicago

Chicago's skyscrappers reminded me a lot of NYC where I went to college. The buildings run from 60 floors to 100 floors! This was my second trip to Chicago, the first was a college graduation gift from my mother to see the Taste of Polonia Festival. How do New York and Chicago compare? Well Chicago is smaller than NYC with only 2.7 million people. The bitter winters makes it a city of drivers, unlike (mostly) car-less New Yorkers. However, Chicago has a beach right in the city! Yes you read that right, I was surprised too. They actually have 26 beaches and my favorite was North Avenue Beach. It has an Ocean Liner inspired building which has a bar on top with a dj and a day party going on. The beach has a ton of volleyball nets and is surrounded by the Lakefront Trail. The Lakefront Trail is an 18-mile path where you can bike, run, or walk adjacent to the beach. It's great for people watching while having a gorgeous view of the beach and skyline. Chicago has an awesome bike sharing system called the Divvy which has 300 stations. I saw so many people on the lakefront trail using the Divvy bikes.

What makes Chicago so beautiful is all the green space, waterfronts and river that flows through the city. Best of all the area around Merchant Mart smells like chocolate! The Blommer Chocolate Factory permeates the air and made walking around smell lovely! Chicago is famous for their deep dish pizza which is cheese on the bottom and chunky tomato sauce on the top. Giordano's would be the most famous restaurant in Chicago to try. You might all know the pizza chain Uno's that came out of Chicago.

Chicago's downtown area is called "The Loop." It got it names from the elevated L train tracks that encircled it. The 'L' is short for "elevated" and all but one of the 8 routes are above ground. In the loop  you can find 22 colleges, every time I turned around I saw another school. You will also find the Riverwalk which is a pedestrian walkway along the river lined with bars and where you can catch the water taxi or rent kayaks.


I bet you didn't know the nickname "windy city" is not because it's windy (which it was), it's because of the politicians who have historically blown hot air in Chicago. When a native Chicagoan told me this I couldn't believe it so I had to google and found out that Chicago is also ranked the most corrupt major city in our country. Think of the corruption of the likes of former Governor Rod Blagojevich former US Congressman Jesse Jackson Jr. In fact six Illinois governors have been charged with crimes and four went to prison.

Chicago has 56 museums! Including the Art Institute of Chicago which is ranked as the best museum in the world.  I went to the Garfield Conservatory which is a gorgeous botanic garden.  I also visited the Adler Planetarium. I walked along the Lakefront Trail to get there which you can see in the super windy picture below.  When I came out of the Planetarium, this view was completely covered in fog!


Last year Chicago got a new ferris wheel at the Navy Pier  that is taller and faster.

This was off the beaten path, but I went to a Walgreens that used to be a bank and this was in its basement, how cool is that!

Where to Eat:
Cindy’s Rooftop - great views of Millennium Park (see pic above)
Real Good Juice - green juices, smoothies and avocado toast (multiple locations)
Sprinkles cupcake - right off of Chicago's Magnificent Mile where all the major shopping is and across from Oak Street beach
Mercadito - upscale Mexican restaurant with 3 locations and unique cocktails
Native Foods - fast casual vegan restaurant chain with 4 locations in Chicago, I visited while I was in LA as well.
Sienna Tavern - modern northern Italian restaurant, best meal I had in Chicago!
The Hampton Social - best brunch spot, amazing cocktails, awesome vibe, nautical theme with a live band and huge open windows creating a nice breeze, drinking a frozen rosé cocktail in the pic below.

I went rooftop bar hopping with friends to find the best view.

Chicago Rooftop Guide
Cindy’s Rooftop
RAISED Urban Rooftop Bar
JR Parker
Cerise (Virgin Hotel)
ROOF on theWit
London House - best view below


    1. I love this post!! I actually live in Downtown Chicago, and I really enjoyed your pictures =) I also LOVE that we have a beach right near the city. So glad you were able to get to North Avenue! That place is definitely hopping! You definitely nailed the food recommendations too =). Those are all my favorites!! Thanks for such a great post about my favorite city!

    2. Great pictures and travel post!! I visited chicago once years before, but during the winter so it wasn't nearly as sunny or pleasant weather wise...although it was still fun.Love all the rooftop bar pictures and suggestions, I wasn't old enough to drink at the time but sure makes me ready to head back and check out the scene :)

    3. I've been trying to talk my husband into moving to Chicago for ages now. This makes me want to go even more!

    4. I love all of your pictures! I haven't been to Chicago in a year or two, but my husband and I are planning on trying to make it up there in the fall (we live in downstate IL). We always stay somewhere off Michigan Ave by Water Tower Place so Giordano's and Sprinkles are two must-haves every time we go!