Things to do in Chicago – Illinois

Must Do

Any visitor to Chicago must go up into the Hancock Building (rather than the Sears Tower). The views are spectacular and instead of paying an admission fee, you can sit in the Lounge and enjoy a cocktail while gazing out at the city.

In 2022 the Avondale area of Chicago was named number 16 in Time Out’s 51 coolest neighbourhoods around the world.

Chicago from the lake Source Flickr

What do you like best about your city?

Chicago has the perfect mix. We have world-class luxury hotels and restaurants, high-end boutiques and beautiful high-rises, but we also have laid back dive bars, cheap places to eat and designer discount shops. You can have a great time in Chicago on any budget.

Chicago Canal Source Flickr

Best Walk

Walking down the Magnificent Mile will be high on any tourist’s to do list. Even if you can’t afford to shop at Chanel, Gucci and Tiffany, browsing and window-shopping make for a fun afternoon. Horse-drawn carriages offer rides around the area’s leafy tree-lined streets. Start at the north end and work your way south to Millenium Park.

Best Restaurants

Chicago has an abundance of upscale restaurants ranging from creative tasting menus at places like Alinea, Tru and Charlie Trotter’s, to traditional steakhouses like Gibson’s and Smith and Wollensky. These famous names don’t come cheap though. Visitors on a tighter budget can get great food and lower prices at one of Lettuce Entertain You’s many restaurants like Ba Ba Reeba Tapas Bar, Mon Ami Gabi French Restaurant and Italian Osteria Via Stato.

View of the city Source Flickr

Best Music/Festival

Lollapalooza is the biggest and best music festival of the summer, but every weekend in Chicago brings another festival. There are festivals devoted to neighborhoods, foods, cultures, arts, music, and more.

Best Nightlife

The Wicker Park and Bucktown neighborhoods offer the most nightlife options in a small area. Options range from dance clubs to dive bars, and everything in between. A very unique Chicago bar is the Violet Hour. It’s marked with no sign, but those who find it are rewarded with tasty classic speakeasy cocktails. Chicago’s gay scene is concentrated in Lakeview, on Halstead Street between Addison and Belmont.

Best Day Trip Out of the City

Milwaukee is an easy two hour drive (or bus or train ride) from Chicago. You can tour several breweries, including Miller, Sprecher, and Lakefront.

Something that not many tourists would know about.

Many restaurants (particularly ethnic restaurants) outside of the downtown area, in neighboring ‘hoods like Lakeview and Bucktown, are BYOB. Customers can bring their own wine or beer to drink, cutting down on dining costs.