Arrive in Chicago and settle into your accommodation. There are tonnes of places to stay in this bustling city; check out some of our top stays in the list below.

Assuming you spend the first day travelling/ settling in, you may have enough time to enjoy the evening in Chicago.

Start off with a night tour of the Chicago River by boat:

⭐ Night Tour with Cocktails

⭐ Creepy Cruise

⭐ Private boats

After your tour, grab some dinner/ drinks.

On Day 2, get out early and hit one of the coffee spots from our list.

Today is for seeing the popular sights of Chicago.

The order in which you do the list below might vary depending on where you are staying/ where you get morning coffee/ breakfast but all are within walking distance of eachother:

⭐ The famous 'Giant Bean' (called Cloud Gate

⭐ Millenium Park

⭐ Chicago Theatre

⭐ Michigan Avenue Bridge (DuSable Bridge)

Along the way, you'll be graced with typical Chicago architecture and photo opportunities for the famous suspended L trains that run above ground.

This evening, book a sunset cruise on Lake Michigan - the view of the Chicago skyline against the water is simply stunning.

After the sunset cruise, head to a rooftop bar for more views of the city by night:

CloudBar at 360

London House Rooftop

RAISED Rooftop

Now you've seen all of the tourist sites of Chicago, on Day 3 let's dive into the real history and soul of the city.

There are 2 options for the daytime today. Both end with the same evening activities.

Option 1:

As with most American cities, black history is foundational to learning their past, giving rise to the significant influence in art, culture, music, food, civil rights, education, businesses, engineering, and politics.

Chicago is no different, and in fact black history is even more critical in its story since Chicago was founded by Jean Baptiste Point du Sable, a black French-Haitian.

Head straight down to South Chicago - Bronzeville specifically, which is considered a 'Black Metropolis' housing a rich Black legacy dating back to the 1800's.

First stop: Bronzeville Winery for brunch.

Next, check out these points of interest in Chicago's south side:

⭐ DuSable Black History Museum

⭐ Obama Kissing Rock - the place where former President Barack and Michelle had their first kiss, for the romance lovers.

⭐ Chess Records Office & Studio

Bronzeville is generally considered safe during the day, however it is not advised to explore at night especially if you don't know the area and if you're alone. Use standard city awareness with keeping valuables out of sight, not venturing far from the main streets etc.

You may wish to join a guided tour instead:

⭐ Chicago Mahogany Tours

⭐ Inside Chicago Walking Tour of Bronzeville

⭐ Underground Railroad Tour

Option 2:

Take the Blue Line (Metro) north westwards out of the central Chicago Loop to visit the trendy neighbourhoods of Wicker Park, Logan Square, and Avondale.

Start with Wicker Park. Grab coffee at La Colombe Coffee Workshop and pastries at Mindy's Bakery.

Afterwards, have a wander down N Milwaukee Avenue where you'll find lots of vintage clothing stores for a spot of shopping. Stock up on Stan's Donuts before leaving Wicker Park.

For beer lovers, make a pit stop at Goose Island Taproom, where Goose Island beer is still brewed after being founded in Chicago in 1988.

Next, head to Avondale which was voted the 5th coolest neighbourhood in the world in 2025. It has an eclectic mix of cultures from Latin American to Polish, so you'll find a great mix of food and art. It also sits on the Chicago River but the river here looks very different to downtown Chicago. Here are some things to do in Avondale:

⭐ Rockwell on the River

⭐ Rent a boat - this part of the Chicago River is much calmer than downtown with opportunities to see local wildlife.

⭐ St Hyacinth Basilica

Finally, head down to Logan Square and wander around this hipster neighbourhood. Here are some options for things to do:

⭐ The 606 Bloomingdale Trail

⭐ Logan Arcade

⭐ Logan Theatre

Your evening will be spent enjoying the deep Chicago-rooted music scene, whether its blues, jazz, house, or hip hop.

Music clubs/ bars are depicted by a musical symbol in the map at the top of this page.

Chicago is home to some great sports teams, and sports is part of the quintessential American experience.

So on your last day catch either a baseball, football, or basketball game (season dependent). Use Ticketmaster for official tickets.

If sports really isn't your thing, use the day to go back an do anything you may have missed or visit somewhere you really liked again.