3-Day Chicago Itinerary: Best Things to Do Downtown in Summer
By
Lynn Celek
on
April 22, 2025
Day 1: City Views From Above & Along the River
Willis Tower & the Chicago River
Morning: Start your day at the Willis Tower Skydeck (locals still call it the Sears Tower). Head up to the Skydeck and step onto The Ledge for a thrilling view.
Cost: $32; expedited entry $55
Best time to go: As with most tourist attractions, lines are typically shortest early in the morning.
Hours of operation: 9am-10pm, daily
Afternoon: Explore the Chicago Riverwalk. Depending on your budget and energy level, you can:
Walk along the river. There are numerous bars and restaurants along the walking path. (The riverwalk is below the street level.)
Take a riverboat cruise. On the low end, you'll pay $28 for a 45 minute cruise, and $45-$50 for 1.5 hours. These tours are great for learning about Chicago's architecture.
Kayak on the river. Wateriders is located right downtown under the Kinzie Street Bridge. Expect to pay $60/person for 2 hours on weekdays and $70 on weekends.
View from Willis Tower.
The Ledge on the Skydeck.
View from Willis Tower.
The Ledge on the Skydeck.
View from Willis Tower.
The Ledge on the Skydeck.
Day 2: Art, Parks, & Comedy
Art Institute of Chicago, Millennium Park, & The Second City
Morning: Art Institute of Chicago
This museum has an incredible collection of Impressionist and Post-Impressionist art.
Hours of operation: Mon, Wed, & Fri-Sun: 11am-5pm; Thurs: 11am-8pm; Tue: Closed
Cost: $32 adult, $26 seniors, $26 teens & students
After: Millennium Park is located directly north of the art museum. Stroll through the park to see The Bean (Cloud Gate) and enjoy the park's gardens and fountains.
Late afternoon: Relax along the lakefront at Pablo's Tiki Snack Shack. The drinks are a little pricey, but you get to sit right on the water.
If you'd rather explore more, walk about 30 minutes south to the Shedd Aquarium. Adult tickets range from from $40-45 depending on day and time.
Apart from the aquarium, you'll also find the The Field Museum of Natural History, 12th street beach, and another spot for drinks and food on the water.
Evening: Jump in an Uber and catch a show at The Second City, Chicago's legendary comedy club where many famous comedians got their start. Make sure to book these tickets in advance.
Me at Pablo's Tiki Snack Shack. (See original map for location.)
Map of alternative sites to visit.
Me at Pablo's Tiki Snack Shack.
Map of alternative sites to visit.
Day 3: Beach Day & Sunset Views
City Beaches & Navy Pier
Evening: Ride the Centennial Ferris Wheel at Navy Pier to watch the sunset. You should purchase tickets in advance to skip the ticket line. The ticket line and the ferris wheel line are separate. (Click on "All Pier Park Attractions" to purchase tickets at the link above.)
The Concrete Beach.
Riding the Centennial Ferris Wheel at Navy Pier.
The Concrete Beach.
Riding the Centennial Ferris Wheel at Navy Pier.
Take a Piece of Chicago Home
3D Wooden Maps by MapCuts
If you fell in love with Chicago's summer vibe—or want a memorable thank-you gift for your host—MapCuts makes handcrafted wooden maps that capture the places that matter most.
What is MapCuts?
We’re a small business that makes laser-cut, layered wood maps of lakes, cities, and coastlines—each one crafted in our shop in Cuyahoga Falls, Ohio. Every map is stained, framed, and assembled by hand.
Our Chicago city map and Lake Michigan map are local favorites. You can also customize a map to show a specific neighborhood or stretch of shoreline.
You’ll get to choose:
✔ Frame size
✔ Standard location or a fully custom map
✔ 8 water stain options to match your style
✔ Frame color: walnut, black, or natural
✔ Custom nameplate text (add a date, quote, or name)
Shipping is free anywhere in the continental U.S.
We’ll send a digital proof before we make your map so you can tweak it until it’s perfect.
