Expecting out of towners but feeling pressured to come up with the perfect weekend itinerary? Luckily, whether it’s your best friend, your parents, a sibling, or first-time visitors, Chicago is practically overflowing with fun and exciting things to do.
We’ve rounded up 5 must-try itinerary ideas to give your next guests the full Chicago weekend experience, with convenient hotel options courtesy of Hilton!
Keep reading to discover what to do and where to stay with your Chicago weekend visitors.
1. Visit Millennium Park
In the heart of downtown, Millennium Park is arguably the city’s most Instagrammable spot and an essential addition to any Chicago visitor’s itinerary. Between interactive fountains and art installations to public greenspace, this urban oasis features so many spectacular attractions, all to the backdrop of lakeshore views.
Unfortunately, the beloved “Bean” sculpture is closed for “necessary maintenance” through 2024, so you won’t be able to show off this legendary landmark to visitors any time soon. But you can still take guests to see Millennium Park’s stunning array of arts and architecture, including the four-season Lurie Garden, the Crown Fountain, along with the Boeing Galleries.
🏨Where to stay: theWit Chicago, a Hilton Hotel is within blocks of Millennium Park, and is a wonderful option for incorporating lots of iconic Chicago activities into your guests’ weekend itinerary.
2. Indulge in the deep-dish experience
Chicago boasts one of the nation’s greatest food scenes. But if there’s one food tourists and locals alike line up for, it’s Chicago’s signature deep-dish style pizza.
Your weekend visitors will likely request a deep-dish pizza recommendation if you don’t supply one yourself, so be prepared to answer the question: “Where’s the best place to get deep-dish pizza in the city?”
For pies that will totally satisfy your out of towners and give them the indulgent experience they’re looking for, check out these three local deep-dish favorites:
- Pequod’s Pizza (2207 N Clybourn Ave., Chicago, IL 60614)
- George’s Deep Dish (6221 N Clark St., Chicago, IL 60660)
- Lou Malnati’s Pizzeria (Find your nearest location)
🏨Where to stay: Pizza lovers should definitely book their stay at Hilton Chicago. Located on Michigan Ave., you’ll find an abundance of South Loop staples within walking distance!
2. Explore Museum Campus
With over 50 museums and cultural institutions to experience in the Windy City, you could easily curate an entire weekend itinerary around these attractions.
However, Chicago’s Museum Campus is a simple way to narrow it down to three worth showing off to your next visitors, each within a hop, skip, and a jump from one another.
The Field Museum, Shedd Aquarium, and Adler Planetarium are all located on Museum Campus. Visiting these three institutions supplies an accessible, day-long itinerary filled with the wonders of the natural world and outer space.
- 🦖Field Museum: This world-famous natural history museum claims to house nearly 40 million artifacts and specimens, including one of the world’s best preserved Tyrannosaurus rex specimens!
- 🐠Shedd Aquarium: The Shedd Aquarium gives visitors the chance to have one-of-a-kind encounters with an impressive 25,000 aquatic entities, among them deep-sea jellies and playful beluga whales.
- 🪐Adler Planetarium: Escape to the stars and discover a host of interactive, out-of-this-world exhibits at the Western Hemisphere’s first planetarium.
🏨Where to stay: Palmer House, a Hilton Hotel’s Adler Planetarium Package is the perfect way to make the most of you and your guests’ visit to Museum Campus. Enjoy overnight accommodations and up to four general admission digital passes to Adler Planetarium, giving you an easy and accessible option for experiencing Museum Campus.
4. Enjoy a river cruise
What better way for out of towners to see all of Chicago’s 26-mile skyline than from the horizon itself? Venture down the Chicago river and on Lake Michigan to soak in mesmerizing city views with a river cruise!
Boat tours are a fantastic opportunity for your guests to immerse themselves in scenic city views during a blissful weekend excursion. From architectural tours to chill brunch cruises, there’s undoubtedly a Chicago river cruise tailor made for everyone.
🏨Where to stay: Cap off your time on the water with aerial views at LondonHouse Chicago, Curio Collection by Hilton. As one of the “Big Four” skyscrapers around the former Michigan Avenue Bridge, its rooms span an adjoining 22-story glass structure and provide incredible riverfront views.
5. Catch a sunset at Navy Pier
After discovering everything Chicago has to offer, head to Navy Pier and wow your guests with a breathtaking sunset.
Catching a sunset at the People’s Pier is a Chicago bucket list staple. And once there, your guests will also have an opportunity to view public art installations, grab a bite to eat, and check out a whole host of Pier Park Rides open on the weekend – including the iconic, 200-foot Centennial Wheel!
🏨Where to stay: If you and your visitors do plan a late night at Navy Pier, be sure to book a stay with Sable at Navy Pier Chicago, Curio Collection by Hilton. Located in the heart of Navy Pier, this elegant accommodation is less than ten minutes from the Magnificent Mile, Millennium Park, and the Wrigley Building. Your out of towners will find stunning skyline views and easy access to so many must-see attractions around the city.
Your visitors are sure to have a blast thanks to these fabulous Chicago weekend itinerary ideas and plenty of Hilton hotel options to suit their needs.