This post contains product affiliate links. These are mainly on items/hotels/tours that I personally endorse & love. I may earn a small commission if you make a purchase, but at no extra cost to you.
Looking for the perfect weekend with friends in Chicago? From deep-dish pizza to skyline views, here’s your complete guide to explore the city.
Chicago is one of those cities that just works for a fun weekend away with friends. From iconic architecture and quirky neighbourhoods to buzzing food scenes and lakeside views, there’s something for everyone.
The city is lively all year round, with seasonal highlights like Christmas markets, summer festivals, and plenty of reliable attractions, so it doesn’t matter when you visit – Chicago never disappoints. With so many options, though, it can be a little overwhelming, so here’s a guide to planning a weekend in the Windy City that’s perfectly tailored for you and your friends.
Pick the perfect location
I always think where you stay can completely shape your trip. The accommodation is so important, so I always put a lot of time and effort searching what’s right for me. I’d suggest sitting down with your friends and figure out what kind of weekend you want.
- City glamour: If you’re after shopping, dining, and late-night adventures, a luxury hotel downtown puts you in the thick of it.
- Exploration-first: If your goal is sightseeing and outdoor fun, a budget-friendly hotel near the attractions you care about most is ideal. You can find a cheap hotel close to the attractions you’re most interested in.
Think about what you want to do, the vibe you’re looking for, and how central you need to be. It makes a big difference when planning routes and meet-up spots.
Exploring downtown and the Riverwalk
Downtown Chicago is a great starting point for any trip. The Riverwalk is a scenic stretch along the Chicago River, dotted with cafes, bars, and public art installations. It’s the perfect place to get your bearings, soak up the city vibe, and admire that famous skyline. Pro tip: Kick off your weekend with a historical river cruise. It’s a fun way to see the city from a completely different angle.
The Riverwalk also works brilliantly as a meeting point if your group splits up while exploring downtown. It’s central, easy to navigate, and full of spots to relax and regroup.
Visiting Millennium Park
No visit to Chicago is complete without Millennium Park. Iconic landmarks like Cloud Gate (aka “The Bean”) and Crown Fountain are perfect for photos. I know this is what I think of when I picture Chicago. They also make a handy rendezvous points for your group!
The park itself is great for picnics, people-watching, or just a peaceful stroll. If you’re a fan of art and culture, the nearby Chicago Cultural Center is worth popping into, while coffee in the mornings is a lovely way to get a feel for the city and watch it come alive. This is a great place to meet new people and catch up with friends while in the city.
Trying Chicago style food
Chicago is, of course, famous for its hot dogs and deep dish pizza, but there’s a lot more to the city’s culinary scene than carbs. Neighborhoods like West Loop and River North offer a diverse range of restaurants that welcome larger groups. If you like trying new cuisines via shared plates, work your way through the sharing platters, tapas, and meze in the city’s many friendly Mexican, Korean, Middle Eastern, and Indian eateries.
Exploring Lincoln Park
Lincoln Park is perfect for a slower pace. The surrounding gardens and lakefront trails give you space to relax, while the neighbourhood is full of cafés and brunch spots to refuel. If you’re up for it, you can extend your walk along the lakefront trail, which offers stunning views of Lake Michigan and some of Chicago’s most famous streetscapes.
Spending time at Navy Pier
Navy Pier is a fun, quirky, and group-friendly location with something to offer everyone. A ride on the Centennial Wheel will give you broad lake and skyline views. Those of you who don’t like heights can enjoy indoor and outdoor dining options, shopping, and short shows. The Chicago Children’s Museum is here, too, if you feel like indulging in some nostalgia.
Exploring Wicker Park and Bucktown
Wicker Park and Bucktown are buzzing with creativity and independent charm. Think record stores, bookshops, quirky boutiques, and walls covered in street art. Cafés and casual restaurants make it easy to take a coffee break while soaking up the vibrant neighbourhood atmosphere. If your group enjoys exploring local culture and discovering hidden gems, these areas are a must.
Enjoying a night out
Chicago is famous for its jazz scene, which is still going strong to this day. You can take in a classic show at a cozy jazz club or, if jazz isn’t your thing, spend your evenings at comedy gigs, late night diners, or rooftop bars with skyline views. If you love live music, your group will find plenty to see in neighborhoods like Wicker Park, Lincoln Park, and West Loop. Comedy fans often choose shows at Second City or Zanies.
General group-friendly activities
Chicago has a lot of ways to keep groups entertained. You can try a kayaking session on the river, a group cooking class, an escape room, and much more. Sports fans can attend a Cubs, White Sox, Bulls, or Blackhawks game depending on the season. If your group prefers a slower outing, you can visit a gallery district or join a neighborhood food tour. Or simply wander around the Downtown and lakefront areas, dipping in and out of museums, shops, galleries, and eateries as you go.
A weekend built for friends
Chicago gives friend groups an ideal mix of skyline views, unique neighborhoods, great food, and waterfront scenery. The city stays easy to navigate when you plan simple routes and choose central meeting spots. Whether your group enjoys parks, food, art, or nightlife, Chicago has options to fit every taste and every energy level.
Chicago is one of those cities that keeps giving. No matter how many times you visit, there’s always something new to see, eat, or explore. Whether you’re wandering the Riverwalk, sampling deep-dish pizza, enjoying a rooftop bar, or simply strolling along Lake Michigan, the city has a way of bringing friends together and creating memories that last long after the weekend ends.
With a bit of planning, central meeting points, and a mix of sightseeing, food, and downtime, your weekend in Chicago will be stress-free, fun-filled, and packed with experiences everyone in your group will love. So grab your friends, put together your itinerary, and get ready for a weekend in the Windy City you won’t forget!
