Chicago, Illinois

April 10, 2018

From skyscrapers and historic landmarks to rooftop views and the best pizza in the US, I’ve rounded up my favorite spots in my beloved hometown city.

Art Institute

111 S Michigan Ave.

The Art Institute of Chicago is one of the oldest and largest art museums in the United States. Home to many famous works of art such as Georges Seurat’s “A Sunday Afternoon on the Island of La Grande Jatte” and Grant Wood’s “American Gothic,” you could spend all day here and not even scratch the surface of every collection.

North Avenue Beach

1600 N Lake Shore Dr.

A summertime Chi destination, North Avenue Beach offers access to Lake Michigan, beach volleyball, restaurants, and a boardwalk where you can ride a bike along Lake Shore Drive. It’s free and open to the public, and although it’s no the Atlantic of Pacific, don’t write it off to quickly. It’s definitely a sight for sore eyes.

Chicago Riverwalk

The Chicago Riverwalk is an open, pedestrian waterfront located on the south bank of the Chicago River that has in recent years began to invest in restaurants. Dine and drink along the river and then walk from Lake Shore Drive to Lake Street while admiring the Chicago architecture from a new level.

Myopic Books

1564 N Milwaukee Ave.

Myopic Books is a treasured gem of Chicago’s Wicker Park neighborhood that has won awards such as “Reader’s Pick – Favorite Used Book Store” from The Chicago Reader and “Best Used Book Store” from Chicago Magazine. The bookstore hosts concerts and poetry nights and offers a collection of 80,000 books. You’ll surely get lost in this three level book heaven.

The Allis at SoHo House Chicago

113 – 125 North Green St.

Perfect for brunch, afternoon tea or any other meal, you can’t go wrong with any of the menus The Allis offers. A two story lounge with floor to ceiling windows and a rustic farmhouse interior, it’s perfect for large or small groups. The best part is you don’t even need to be a member of SoHo House to reserve a table.

Summer House Santa Monica

1954 N Halsted St.

Summertime Chi is the most glorious times of year but only lasts about 4 months. Summer House Santa Monica transports you instantly into a sunny state of mind no matter what time of year you visit.

Lou Malnati’s

1120 N State St.

You can’t go to Chicago without getting a slice of deep dish pizza and Lou Malnati’s is a Chicago classic. There are several locations throughout the city but if deep dish doesn’t peak your interest they also offer thin crust. Other pizza favorites include Parlor Pizza, Chicago Pizza and Oven Grinder and Connie’s Pizza.

The Signature Room at the 95th

875 N Michigan Ave.

The Signature Room at the 95th is located on the 95th floor of the John Hancock skyscraper and takes dinner with a view to a whole new level. White tablecloths, upscale American fare and specialty cocktails, this is the perfect place for an dates and celebrations of any kind. After dinner, head upstairs to the 96th floor to the Signature Lounge for a night cap and some more views.

3 Arts Cafe at Restoration Hardware

1300 N Dearborn St.

Talk about interior goals. Perfect for drinks and small bites, the 3 Arts Cafe sits in the Restoration Hardware Chicago Gallery which took over Chicago’s Historic Three Arts Club which was a home and club for women in the “three arts” of music, painting and drama in the 1900s. After some drinks, walk around the 4 story landmark converted gallery and get your fix of design inspo.


1112 N State St.

Set on the site of the 1920’s era famed Cedar Hotel and adjacent to the Viceroy Hotel, Somerset offers traditional American fare, excellent service and great cocktails.

Beacon Tavern

405 N Wabash Ave.

Beacon Tavern offers great seafood and is your go-to riverside dining experience. Located along the Chicago River and steps from the Magnificent Mile, it is perfect for lunch before a day of shopping or dinner and drinks.

Cindy’s Rooftop

12 S Michigan Ave.

Specializing in one of a kind and Instagram-worthy cocktails, enjoy your drink while overlooking Millennium Park. You can also eat at Cindy’s Rooftop, which sits on the penthouse of the Chicago Athletic Association, but it has limited seating and is always booked so reserve your table well in advance. This is easily my favorite spot for drinks with a view in all of Chicago.


100 W Ontario St.

A fast food chain that compares to no other, Portillo’s is home to the best Chicago dogs, Italian beef, chopped salad and chocolate cake. When in need of a quick bite Portillo’s never disappoints.



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