7 things to do in Chicago with friends

Pick your plan

1. 1. Walk the Riverwalk before lunch

   

   The Riverwalk gives you a first look at Chicago without buying a ticket. Walk along the water from Michigan Avenue toward Wells Street, stopping when a building or a passing boat catches your eye. An optional lunch afterward makes this an easy plan for friends arriving at different times.

   The practical details

   • Suggested walk: start at Michigan Avenue and follow the river west toward Wells Street. Give yourselves an hour, including photo stops.
   • If you have a cruise booked, walk first and finish back near its dock. Keep a coffee stop optional so late arrivals have a clear place to join.

   Planning budget per person$0 to $20

   Choose Chicago

2. 2. See Chicago from an architecture cruise

   

   For a closer look at the buildings along the river, take the Chicago Architecture Center cruise aboard First Lady. The 90-minute trip can anchor the afternoon: walk before boarding, then find lunch after. Book the same departure for everyone and check the operator’s weather and cancellation terms.

   The practical details

   • The CAC cruise lasts 90 minutes. Its dock is at the southeast corner of the Michigan Avenue Bridge and Wacker Drive; use the operator’s directions to reach river level.
   • Our suggested schedule: arrive 30 minutes before departure, then leave another 30 minutes after the sailing before a lunch reservation.

   Planning budget per person$60 to $90

   Chicago Architecture Center

3. 3. Spend a free morning at Lincoln Park Zoo

   

   Lincoln Park Zoo is a useful starting point for a day with no admission charge. Pick two or three areas that interest the group and leave the rest for another visit. The neighboring conservatory makes a natural second stop, especially if you want some time indoors.

   The practical details

   • Choose two or three areas on the zoo map and allow two hours rather than trying to cover the whole site. General admission is free; ticketed events and extras are separate.
   • Pair it with the conservatory next door. Check both schedules before deciding which one comes first.

   Planning budget per person$0 to $20

   Lincoln Park Zoo

4. 4. Step inside Lincoln Park Conservatory

   

   Lincoln Park Conservatory gives a rainy afternoon somewhere to go. Book a free timed entry, spend 45 minutes to an hour inside, then decide whether to continue to the zoo or stop for lunch. Keep the park walk optional so the plan still works if the weather stays wet.

   The practical details

   • Address: 2391 North Stockton Drive. Admission is free, but reserve a timed entry through the conservancy.
   • Allow 45 to 60 minutes for a first visit. For a mixed-budget afternoon, follow it with the zoo or a short park walk instead of another ticket.

   Planning budget per person$0 to $15

   Lincoln Park Conservancy

5. 5. Picnic at North Avenue Beach

   

   After Lincoln Park, make North Avenue Beach the lunch stop. Bring individual sandwiches, a snack to share and a layer for the lake wind. Set up off the Lakefront Trail so cyclists and runners can pass. In cold weather, keep the lake visit short and eat indoors afterward.

   The practical details

   • Allow an hour for lunch and a short walk. Check trail work and beach notices before leaving.
   • Swimming is seasonal and only permitted in designated areas with lifeguards on duty. A picnic plan should not depend on being able to swim.

   Planning budget per person$10 to $20

   Chicago Park District · North Avenue Beach

6. 6. Share a deep-dish at Lou Malnati’s

   Lou Malnati’s at 439 North Wells Street gives a River North afternoon somewhere to end. Agree on toppings and ask how many deep-dish pizzas suit the table; these are more filling than thin slices. Order a salad to share if you want something while the pizzas cook.

   The practical details

   • Set aside 90 minutes as a planning allowance and ask about the current wait before sitting down. Contact the restaurant for a large table.

   Planning budget per person$25 to $45

   Lou Malnati’s · River North

7. 7. Catch a Second City show in Old Town

   

   End the day with a Second City show in Old Town. The Chicago Mainstage is at 1616 North Wells Street; choose a performance from the current calendar and plan dinner nearby. Read the room name on the ticket, since the company has more than one performance space.

   The practical details

   • Book one performance and seating category for the whole group. Check age rules and the arrival time on that show’s booking page.

   Planning budget per person$25 to $65

   The Second City · Chicago

Planning estimates per person in US dollars, not venue quotes. They cover the activity and food described; transport, taxes, tips and extra purchases are separate. Check current admission prices, opening times and reservation terms before you go.