Top Picks for Chicago for First Timers

November 30, 2017 0 Comments

There are so many amazing things to do in Chicago it is hard to know where to start. Here are my top picks for a first timer traveling to Chicago.

Favorite Bars with a View:

Signature Lounge

The Signature Lounge is on the 96th floor of the John Hancock Building downtown Chicago. The views at sunset and at night are breathtaking! I would definitely recommend skipping the touristy Skydeck Chicago located at the Willis Tower and heading to the Signature Lounge to get a cocktail instead. It is free to enter the Signature Lounge, however, you are required to buy a drink to get into the main bar area with all of the views. Make sure to check out the lady’s restroom as the views are some of the best in the house! The entrance is separate from the 360 Chicago attraction, also located in the Hancock Building, so be sure to ask where to get in line. The line can be quite long, but I thought the views were worth the wait.

Cindy’s Rooftop

Cindy’s Rooftop overlooks Millennium Park and Lake Michigan. There is an amazing view of the Bean and city skyline from the open air terrace. Cindy’s felt very stylish/trendy. I could definitely picture myself hanging out there with friends if I lived in Chicago for real. I really enjoyed the vibe of the place. It was less touristy than the Signature Lounge and is the perfect spot for Instagram junkies.

Favorite Restaurants:

Pizzaria Uno

Chicago deep dish pizza! Pizzeria Uno claims to have invented the deep dish pizza. I have no idea if this is true. All I know is that it was SO good. The atmosphere was really neat as well. It felt like a hole in the wall pub, even though it is quite famous. Warning: do not go when you are super hungry. It takes 45 minutes for the pizza to be made and there will most likely be a wait. However, the hostess will take your order as soon as you arrive so they can get your pie cooking. If Pizzeria Uno seems too busy, you can always check up the street to Pizzeria Due which was created to expand the restaurant.


Eataly is a market , cafe, restaurant and bar all rolled into one. At Eataly you can sit down and eat at a counter, eat some fancy food, sip on some vino or buy food to cook at home. The great thing about Eataly is that there are so many choices to fit your needs.


Portillo’s is a lively restaurant known for its Chicago style dogs. It is a casual establishment with impressively cheap beer for the Chicago downtown area. Hot dogs aren’t the only thing on the menu. They serve pasta, salads, sandwiches and burgers.


Favorite Parks:

Millennium Park

Millennium Park is home to “the Bean”. The Bean, or Cloud Gate, is such an awesome place for snapping selfies and a fun place for serious photography. The park also houses an ice skating rink open in the winter months, a climbing wall/playground area and the Lurie Garden. The BP Bridge and the Pritzker Pavillion are two innovative architectural focal points of the park which also make for great photo ops. 

Milton Lee Olive Park

I found the Milton Lee Olive Park by accident while exploring one day in Chicago. It is located to the left of the entrance to Navy Pier. While the park is quite small, it offers a panoramic view of the Chicago skyline and is a great spot for photography and picnics!

Favorite Walks:

The Magnificent Mile

Named one of the Top 10 Shopping Avenues by the National Geographic, the Magnificent Mile (North Michigan Avenue) holds more stores and restaurants than you can count! Drew’s Candy Shop (pictured below) was by far my favorite retailer to explore. If you want to experience in the hustle and bustle of city life, then the Magnificent Mile is the place for you. If shopping is not your thing, I would still recommend taking a stroll on the avenue just to have the experience. 

The Chicago Riverwalk

The Chicago Riverwalk is a neat way to see the city from a different vantage point. Be sure to stop by the City Winery where you can grab a drink in a transparent igloo and admire the city skyline. I walked along the Riverwalk several times while in Chicago as it was very close to my hotel.

Favorite Tour:

Architecture River Cruise

I went on a riverboat tour with Chicago First Lady Cruises. The Chicago Architecture foundation provides the volunteer guides for these cruises so you know they are super passionate about what they are teaching. I really enjoyed learning about the different eras and styles of architecture that came together to create the beautiful city of Chicago. The photo ops weren’t bad either. My favorite part was when we made it all the way out to Lake Michigan and were able to see the entire Chicago skyline. 

One Thing I Missed

Museum of Science and Industry

I heard amazing things about the Museum of Science and Industry in Chicago. Due to my time restrictions, I was not able to go. I was told that in order to fully enjoy the museum you should set aside 3 to 4 hours. I hope to get the chance to visit the next time I’m in the windy city!

Leave a Reply