The windy city, known for great food and incredible architecture, has so much to offer any visitor. This itinerary is completely walkable, with beautiful views all along the way.

For details, hotel and food recommendations, check out our 4 Day Chicago Itinerary

Start your Chicago trip with a river boat cruise, learning the history and architecture of the city. Spend some time exploring Millennium and Maggie Daley Park, finishing off the day with a sunset walk along the lakeshore.

Shoreline Sightseeing River Boat Tour- Learn the history of the city through an architecture tour along the river. Take a nighttime cruise on a Wednesday or Saturday during the summer to watch the fireworks at the end of the tour. 

Millennium Park- Visit the famous “Bean” for a unique photo opportunity. Lots of concerts and special events take place here, so be sure to check out their calendar of events.

Maggie Daley Park- Adjacent to Millennium Park, Maggie Daley has a number of fun activities and areas to enjoy.

Spend the day learning about natural history at the Field museum. (The Shedd Aquarium and Art Institute of Art are also great alternatives.) Next, enjoy the green space of Grant Park, or check out some shopping on Michigan Avenue. In the evening, take in one of the shows running in the theater district

Field Museum- From Egyptian mummies to SUE (the most complete Tyrannosaurus rex ever discovered), the Field museum is a great option for any natural history fans. 

Grant Park- Home to one of the largest fountains in the world, Buckingham Fountain. Each hour, a twenty minute water display reaches heights 150 feet in the air. 

Michigan Avenue- With shops lining the street, including tucked away malls, Michigan Avenue has you covered if shopping is your goal. 

Broadway in Chicago- With so many shows to choose from in the theater district, choose a show that best fits your group. They will not disappoint. 

A more budget friendly day with a neighborhood feel. Spend the day around Lincoln Park Conservatory and Zoo, followed by a night out at the Second City comedy club. 

Lincoln Park Conservatory- Built in 1877, the conservatory and surrounding gardens are free to enjoy but reservations are required.

Lincoln Park Zoo- This zoo has been completely free since its opening in 1968. With over 200 different species, expansive gardens, and conservation efforts, this is well worth a visit.

Second City- This improv comedy club is where some of the most famous comedians got their start- Bill Murray, Dan Aykroyd, Steve Carell just to name a few. There is an age limit of 13 and up. Children between 13-17 must be accompanied by an adult.

Spend the day in the West Loop, starting at a unique spa experience, followed by a fun game of mini golf, ending the day with a movie at an outdoor rooftop cinema.

Aire Ancient Baths- Housed in a historic industrial building, enjoy some time at the baths. This spa designed as the ancient baths of Roman times, offers a number of different pools, saunas, salt baths, cold plunges and more.

Puttery- This can be an especially great option on a cold or rainy day, with a well-themed indoor mini-golf course and bar.

Rooftop Cinema Club- Watch a movie among the lights of the city in a cozy Adirondack chair at this outdoor cinema