While called the Second City only as a nickname, Chicago boasts first-rate architecture, stunning views, delicious restaurants, renowned museums, amazing festivals, and some of the best sports teams in the country. No matter what brings you to Chicago, with almost 200 neighborhoods there’s a unique corner of the city for everyone. This guide offers a fun look at the Windy City, and is sure to blow you away!
Nomad’s Guide to Chicago
Born and raised in the suburbs of Chicago and now living in the city, Chicago is home. I love exploring the city and taking photos, trying new restaraunts and coffee shops, and reading by the lake! When not out in the city, I work in marketing and social media for a candy company. ~@annienbelle
EAT HERE
Italian Restaurants
Chicago is overflowing with Italian restaurants with a few delicious faves being Club Lucky, Trivoli Tavern, Topo Gigio, Monteverde.
Italian Restaurants
Chicago is overflowing with Italian restaurants with a few delicious faves being Club Lucky, Trivoli Tavern, Topo Gigio, Monteverde.
Chicago Pizza
It may be a cliche, but a trip to Chicago isn’t complete without deep dish! Try Lou Malnati’s or Peqouds! If deep dish isn’t your thing, get tavern style from Bungalow by Middle Brow on Tuesdays or Pat’s!
Little Bad Wolf
While Chicago might be known for pizza, the burger game is top knotch as well. Take a trip up north to Andersonville and try this amazing burger paired with a great cocktail.
While Chicago might be known for pizza, the burger game is top knotch as well. Take a trip up north to Andersonville and try this amazing burger paired with a great cocktail.
Sushi Dokku
A moody sushi restaurant in the west loop with a speakeasy bar in the basement.
DRINK HERE
Cindy’s Rooftop
For delicious cocktails with a stunning view above Millennium Park and the Lake, visit this bar inside the Athletic Association hotel. If it’s busy, go to the hotel lobby and play some games at The Game Room.
Cindy’s Rooftop
For delicious cocktails with a stunning view above Millennium Park and the Lake, visit this bar inside the Athletic Association hotel. If it’s busy, go to the hotel lobby and play some games at The Game Room.
Lux Bar
Grab a high top table in the bar and people watch with a delicious dirty martini!
Grab a high top table in the bar and people watch with a delicious dirty martini!
Lazy Bird
This speakeasy style bar in the basement of The Hoxton hotel has amazing cocktails and live music.
This speakeasy style bar in the basement of The Hoxton hotel has amazing cocktails and live music.
A Local Brewery
Chicago has hundreds of different breweries offering local and craft options! A few great ones include Goose Island or Half Acre.
Chicago has hundreds of different breweries offering local and craft options! A few great ones include Goose Island or Half Acre.
STAY HERE
Palmer House
If you’re looking to stay in the Loop (aka the main downtown of the city) this is a great option close to the water and park.
If you’re looking to stay in the Loop (aka the main downtown of the city) this is a great option close to the water and park.
The Hoxton
Located in the West Loop and close to tons of restaurants, shopping, and nightlife - this is a great option for a something outside downtown.
The Peninsula
In River North, near great restaurants and shopping is this luxury hotel. If you’re looking for a spa - this is a go-to!
Sawada Coffee
Located in the West Loop, this coffee shop has one of the best matchas in the city! Or try their famous military latte (matcha with a shot of espresso).
Heritage Coffee + Outpost
With a few spots in the city, and one located inside a bike shop, this is a great spot to get work done or spend an afternoon reading.
Goddess and the Baker
Great specialty coffee and pastries!
Great specialty coffee and pastries!
EXPLORE HERE
Chicago Architecture Boat Tour
Spend an afternoon on the water and take in the history of Chicago’s amazing architecture! A true can’t miss activity.
Chicago Architecture Boat Tour
Spend an afternoon on the water and take in the history of Chicago’s amazing architecture! A true can’t miss activity.
The Art Institute
Spend a rainy afternoon getting lost inside this incredible museum! The Art Institute boasts quite the collection – a go-to is the miniatures exhibit in the basement.
The Bean
Though officially called Cloud Gate, no trip to Chicago is complete without visiting this odd piece of art and getting a selfie.
Though officially called Cloud Gate, no trip to Chicago is complete without visiting this odd piece of art and getting a selfie.
Lakefront Trail
Depending on the weather, either spend the afternoon at beach or rent a Divi bike to explore up and down the lake!
Depending on the weather, either spend the afternoon at beach or rent a Divi bike to explore up and down the lake!
See a show
Whether you’re a fan of musicals, plays, live music or comedy, you’ll find it in the city. Also, Chicago is home to Second City, a comedy club that has launched the careers of many famous comedians!
Whether you’re a fan of musicals, plays, live music or comedy, you’ll find it in the city. Also, Chicago is home to Second City, a comedy club that has launched the careers of many famous comedians!
Catch a game
From baseball in the summer to hockey in the winter, there’s always a sporting event to see! Wrigley Field is also a historical landmark and you can’t beat enjoying a classic Chicago hotdog at the ball game.
From baseball in the summer to hockey in the winter, there’s always a sporting event to see! Wrigley Field is also a historical landmark and you can’t beat enjoying a classic Chicago hotdog at the ball game.
Visit a new neighborhood
Get outside the bustling downtown and visit a Chicago neighborhood. From Lincoln Park up north, to Wicker Park on the north west side, there’s many to choose from and each offers a different vibe.
Get outside the bustling downtown and visit a Chicago neighborhood. From Lincoln Park up north, to Wicker Park on the north west side, there’s many to choose from and each offers a different vibe.
