City Guide: Chicago

When I did a recent poll on Instagram to ask you guys what you wanted to read on the blog, we had a massive response for city guides and travel tips. Since I’ve been to Chicago twice in the past three months, it was only fitting to start here. Chicago is a huge city, so I’m splitting this guide in half more or less with a guide to The Loop, Millennium Park and Grant Park and a guide to Lincoln Park, Wicker Park and Humbolt Park areas.


The Loop is what most people think of when they think of Chicago as home to The Bean, the river walk, deep dish pizza, and more. The further north area of Chicago offers Lincoln Park, Wicker Park, and Hubolt park and is personally my favorite area— it’s more trendy and less touristy, but also more spread out.


+ The Art Institute of Chicago

I love art and the Art Institute of Chicago is so unbelievable you must go see it for yourself. Tickets are a little on the pricey side, but let you visit as much as you want in one day and there’s a student discount. Give yourself at least two hours to see this one!

+ The Doughnut Vault

Just the most incredible doughnuts you’ll ever eat in your life.

+ The Aviary

The Aviary is a swanky cocktail bar owned by Grant Achatz, a world-renowned chef and personal favorite of mine. He believes that cooking is an art and just as a painter isn’t constrained to a canvas, a chef shouldn’t be constrained to a plate. His cocktail art will wow you big time.

+ Open Books West Loop

With two locations and an incredible mission to transform lives through literacy, Open Books is a trendy bookstore and coffee shop.

+ Little Goat Diner

Little Goat is the sister restaurant to the infamous Girl and the Goat and is a must while you’re in Chicago. It’s a fast casual restaurant but often books up hours in advance, so make a reservation on Open Table. Do yourself a favor and order the hot crab dip.

+ High Five Ramen

With only 12 seats in the restaurant, guests line up for hours to get a bite at High Five. Delicious noodles and cocktails in a trendy basement setting.

+ RM Champagne Salon

An outdoor/indoor cocktail bar with small plates in a tucked away alley next to High Five Ramen. Twinkle lights and delicious drinks.

+ Rider For Life

A very cool gift and women’s clothing store featuring ethical and sustainable brands.

+ Gather Home & Lifestyle

Similar vibes to Rider for Life with vintage clothing selections, beautiful plants, local brands, and more.

+ Navy Pier

Definitely the more touristy part of town, but a blast nonetheless. Huge pier downtown with lake views, restaurants, music, and a Ferris wheel. Especially great for real kids and kids at heart!

+ Cloud Gate (“The Bean”)

The Bean is an art installment built to reflect the skyline of Chicago from every direction. Always swarming with tourists, but definitely worth a visit. Right in the center of Millennium Park. Free attraction!

+ Chicago Yacht Club
The Chicago Yacht Club is home to stunning yachts, sailboats, and more and sits nestled on the Chicago River Walk. Walk alongside Lake Michigan and look at the beautiful boats!

+ Museum of Contemporary Photography
A small museum inside Colombia College, this museum features rotating photography exhibits and is free to visitors.


+ Front Bar
A trendy bar inside Steppenwolf Theatre company that serves apps, coffee and cocktails day and night. Visit for a drink or stop by and see a show!

+ Art Effect

A trendy gift shop near Lincoln Park with unique Chicago landmark posters, gifts for kids and adults, and more.

+ Divvy Bikes

You can rent Divvy’s in almost every inch of Chicago, but we loved doing this in the Lincoln Park area as it’s more spread out and less tourist-saturated, making riding bikes much more enjoyable. Bike lines are on most major roads as are sidewalks! Ride for fun or ride to your destination for as cheap as $3 a trip.

+ Wrigley Field and Wrigleyville

Watch the cubs play or just grab a beer at your local bar!

+ Fat Rice

Honestly one of the coolest Asian restaurants I’ve ever eaten at. Get the dumplings.

+ Ipsento 606

Ipsento 606 is a modern coffee shop near Wicker Park with a Central Perk-vibe original location further down the road. Delicious coffee and cocktails and cool people. The Ipsento latte is my favorite!

+ Antique Taco

Another cute Wicker Park spot, Antique Taco serves unique tacos and yummy margaritas and was featured on the list of 50 best tacos in America by Business Insider. Outdoor seating as a plus!

Have any faves that we missed out on? Send us an email and let us know. :) Enjoy the Windy City, friends!


TravelLydia Kerr