Chicago is such an easy drive from the Milwaukee area — which makes Chicago great for a day trip or a weekend getaway! There is so much to see and do, we’ve rounded up some of our top picks (and insider tips!).

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Our Top 20 Picks

Navy Pier

Navy Pier is where you go in Chicago for events, free public programs, attractions, culture, dining, shopping and more. It’s like a city in itself and has so much to do. You can take a sightseeing cruise – ride some rides (like the giant Centennial Wheel), there is so much to do in this iconic Chicago destination!

Chicago Children’s Museum

Chicago Children’s Museum is located at the Navy Pier. And if you have a museum membership here, they may be part of the reciprocity agreement!

Sugar Factory – Chicago and Rosemont

For my kids – the Sugar Factory is a ‘must-stop’. And it’s just what it sounds like!

Shedd Aquarium

The Shedd Aquarium is one of the largest indoor aquariums in the US – holding over 30,000 animals!

Art Institute of Chicago

The Art Institute of Chicago is one of the world’s great art museums, housing a collection that spans centuries and the globe.

Adler Planetarium

The Adler Planetarium is America’s first planetarium and a premiere resource for inspiring the next generation of space explorers.

Field Museum

The Field Museum is one of the largest natural history museums in the world. World-renowned items on display include Egyptian mummies, the man-eating lions of Tsavo, and SUE, the largest and most complete Tyrannosaurus rex ever discovered—and there is so much more in the research collections.

Millennium Park

The Millennium Park Campus is the heart of Chicago. People gather here to picnic in the grass, cool off in the fountain, catch free concerts and movie screenings… and be sure to grab a photo by the big ‘bean’!

Maggie Daley Park

Another MUST STOP — Maggie Daley Park is a 20-acre public park in the Loop community area of Chicago. It has mini golf, climbing wall, a giant playground and more!

Lincoln Park Zoo

Lincoln Park Zoo has FREE admission – making it a must-stop.

Garfield Park Conservatory

Garfield Park Conservatory is one of the largest and most stunning botanical conservatories in the nation. Often referred to as “landscape art under glass,” the Conservatory showcases thousands of plant species from around the world throughout eight indoor display gardens.

Chicago Botanic Garden

Chicago Botanic Garden features 385 acres of landscaped gardens displaying millions of plants & flowers in a variety of settings.

Willis Tower

Formerly known as the Sears Tower – the Willis Tower offers spectacular views spanning up to four states, a one-stop Chicago experience full of interactive exhibits and the famous glass ledge… we dare you to look down…!

360 Chicago

360 Chicago is an observatory on the 94th floor of the John Hancock Building with a tilting glass lookout 1000 feet up!

Blue Man Group Chicago

Blue Man Group Chicago is a comic musical & artistic show featuring lots of audience interaction with the blue-painted cast.

American Girl Store

Located in Water Tower Plaza – it is the largest American Girl store in the US. Not only does it offer a wide selection of American Girl dolls and accessories, but children can have tea with their dolls and have their pictures taken with them.

Wrigley Field

Nothing says iconic Chicago, like a Cubs game at Wrigley Field!

iFLY Indoor Skydiving

You can experience the sensation of flying in the state-of-the-art vertical wind tunnels. Safe for all ages, experience levels and abilities!

Urban Adventure Quest

It’s an urban Scavenger Hunt. It’s a 3-hour Amazing Race. It’s an interactive Adventure Tour, guided from any Smart Phone.

Comedy Sportz Chicago

Comedy Sportz Chicago is an all-ages comedy-as-a-sport, complete with referee, with two improv teams competing for applause!

Other Museums worth Noting

  • Peggy Notebaert Nature Museum
  • Chicago Museum of Science and Industry
  • Bronzeville Children’s Museum
  • Brunk Children’s Museum of Immigration
  • Busy Beaver Button Museum
  • Museum of Illusions
  • WNDR Museum
  • National Museum of Mexican Art
  • Chicago History Museum
  • American Writers Museum
  • Chicago Sports Museum
  • Chicago Architecture Center


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