Nomad’s Guide to Chicago

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!

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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.
 
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!

Nookies
A BYOB cozy breakfast in Old Town is the perfect treat to fuelling days exploring the city!

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.

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.


 
Lux Bar

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.

 
 
A Local Brewery

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.

 
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!

 
GET A COFFEE HERE

Hero Coffee

Enjoy a Teddy Graham or Lavender Latte and a breakfast bagel.


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!
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.

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.

Lakefront Trail

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!

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.

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.