Chicago City Guide

Set along the shores of Lake Michigan, Chicago is a vibrant metropolis renowned for its magnificent architecture, world-class museums, diverse culinary scene and 77 unique neighborhoods to explore from Bridgeport to Logan Square. The city effortlessly blends urban sophistication with Midwestern charm that you just can’t find anywhere else. It has a great public transportation system, so you can explore all the city has to offer at ease. We’ve put together a list of our favorite places to visit and things to do to help inspire you while visiting the windy city.

Millennium Park

The Bean in Chicago with people around it

Start your Chicago adventure with a visit to Millennium Park, home to the famous Cloud Gate sculpture, also known as "The Bean." It's a great spot for taking photos and enjoying the city skyline.

Art Institute of Chicago

Couple walks in front of lion statue at Art institute of Chicago

Next, head to the Art Institute of Chicago, one of the oldest and largest art museums in the United States. Explore its vast collection, including famous works by artists like Grant Wood, Edward Hopper, and Vincent van Gogh.

Navy Pier

Navy Pier wheel cart with flowers in front

Experience fun and entertainment at Navy Pier, offering attractions like the Centennial Wheel, Chicago Children's Museum, IMAX theater, and various dining options with scenic views of Lake Michigan.

Fulton Market

Girls posing in front of neon sign at Fora restaurant in Chicago

Fulton Market is renowned for its vibrant food scene, with a plethora of acclaimed restaurants, cafes, and eateries dotting the streets. From Michelin-starred dining establishments to casual gastropubs and artisanal bakeries, there's no shortage of culinary delights to discover in Fulton Market. Stay in Level Fulton Market, and hit up our favorite brunch spot Fora, pictured above, while you're there.

Magnificent Mile

Michigan Avenue in Chicago shop bloomingdales

Shop till you drop on Michigan Avenue, known as the Magnificent Mile. This upscale shopping district is home to luxury boutiques, department stores, and iconic landmarks like the historic Water Tower.

Chicago River Architecture Tour

Chicago river architecture tour

Discover Chicago's architectural marvels on a boat tour along the Chicago River. Learn about the city's skyline, iconic buildings, and the history behind its architectural innovations.

Deep dish pizza

Deep dish pizza in Chicago

You can't visit Chicago without trying its famous deep-dish pizza. Head to Giordano's, Lou Malnati's – a quick 5-minute walk from Level River North, or Pequod's Pizza for a taste of this cheesy, saucy delight.

Chicago-style hot dogs

Chicago style hot dog

Sample a classic Chicago-style hot dog, topped with mustard, onions, sweet pickle relish, a dill pickle spear, tomato slices, sport peppers, and celery salt, served on a poppy seed bun. Portillo's and Superdawg Drive-In are popular spots for this iconic dish. Or try the “best gourmet-take” on a Chicago Dog by @danthebaker - he combines a Vienna Beef dog with crunchy relish, whole grain mustard, sun-dried tomatoes, and a French gherkin pickle before wrapping it into a classic butter-croissant pastry.

Jazz and Blues clubs

Murial of jazz artist with guitar on building in Chicago

Immerse yourself in Chicago's vibrant music scene by visiting jazz and blues clubs like Green Mill Cocktail Lounge, Buddy Guy's Legends, and Kingston Mines for live performances and a taste of the city's musical heritage.

Old Town

Old town Chicago murial

Old Town is a historic and charming neighborhood located on the Near North Side of Chicago. It's known for its tree-lined streets, Victorian-era architecture, and lively atmosphere. Laugh the night away at Second City, where many famous comedians got their start. Enjoy improv and sketch comedy performances that promise endless entertainment. The best part? You can stay here with us at Level Old Town.

Wrigley Field

Baseball cap at Wrigley Field

Baseball fans shouldn't miss the chance to catch a game at Wrigley Field, home of the Chicago Cubs. Even if it's not baseball season, you can take a guided tour of this historic ballpark to learn about its rich history.