Illinois · best-of list
16 Top Things to Do in Illinois
All 16 things to do our route editors picked in Illinois, across 3 destinations, gathered in one list. 15 come with an insider tip, and 8 cost nothing to visit.
Our curated picks
16 things to do in Illinois, grouped by destination. Destinations with the most picks come first; this is not a ranking.
Chicago 10 picks
Art Institute of Chicago
Chicago · On our Chicago & Great Lakes route
Huge collection including Nighthawks, A Sunday on La Grande Jatte and the Thorne Miniature Rooms.
Tip: Allow at least 3 hours; the Modern Wing links to Millennium Park.
Photo: User:TonyTheTiger · CC BY-SA 3.0
Chicago Architecture Center River Cruise
Chicago · On our Chicago & Great Lakes route
90-minute docent-led boat tour of the skyscrapers along the Chicago River.
Tip: Book ahead in summer; sit on the top deck.
Photo: Chicago's First Lady Cruises · Google
Goodman Theatre
Chicago · On our Chicago & Milwaukee route
Chicago's oldest nonprofit theater, staging A Christmas Carol every holiday season since 1978.
Tip: Book by early November for weekend shows.
Photo: ajay_suresh · CC BY 2.0
Lincoln Park Zoo ZooLights
Chicago · On our Chicago & Milwaukee route
The city's free zoo turns into a light show with millions of bulbs from late November to early January.
Tip: Book a timed ZooLights entry for weekend nights; weekdays are quieter.
Photo: Christine Zenino · CC BY 2.0
Maggie Daley Park Skating Ribbon
Chicago · On our Chicago & Milwaukee route
A quarter-mile loop of ice winding over the hills of Maggie Daley Park, with the skyline rising behind it.
Tip: Reserve a skate time online on weekends.
Photo: Alanscottwalker · CC BY-SA 4.0Magnificent Mile
Chicago · On our Chicago & Milwaukee route
Michigan Avenue's shopping stretch north of the river, with about a million lights strung through its trees in winter.
Tip: Walk north from the river to the Water Tower after dark, then warm up in one of the hotel lobbies.
McCormick Tribune Ice Rink
Chicago · On our Chicago & Milwaukee route
Free outdoor rink in Millennium Park next to Cloud Gate, open from mid-November into March; skate rental extra.
Tip: The city's Christmas tree stands in Millennium Park nearby.
Photo: Adam Jones · CC BY 2.0
Millennium Park
Chicago · On our Chicago & Great Lakes route
Cloud Gate, Crown Fountain and free summer concerts at Pritzker Pavilion.
Tip: See Cloud Gate early morning before crowds.
Photo: Ken Lund from Reno, Nevada, USA · CC BY-SA 2.0
Navy Pier
Chicago · On our Chicago & Great Lakes route
Lakefront pier with the Centennial Wheel, boat tours and skyline views.
Photo: Hbodine · CC BY-SA 4.0
Skydeck Chicago
Chicago · On our Chicago & Great Lakes route
Glass ledges 103 floors up in Willis Tower.
Tip: Buy timed tickets online; clear afternoons have the longest views.
Photo: Evan Huang · Google
The Loop & Chicago River 4 picks
Art on the Mart
The Loop & Chicago River · On our Chicago New Year's Eve route
Large-scale projections across the Merchandise Mart's river facade; on Dec 31 it becomes the countdown clock for the fireworks.
Tip: Watch from the Riverwalk or the Wells Street side of Wacker Drive for a straight-on view.
Chicago River NYE Fireworks
The Loop & Chicago River · On our Chicago New Year's Eve route
The city's free midnight show, fired from the river bridges between Orleans Street and Columbus Drive; held in 2024 and 2025.
Tip: Best views are on Upper Wacker Drive between McClurg Court and Franklin Street; arrive by 11 pm.
Photo: Monk - Ihar Mahaniok · CC BY-SA 3.0
Chicago Riverwalk
The Loop & Chicago River · On our Chicago New Year's Eve route
A 1.25-mile promenade along the main branch of the river, lined with cafes, boat docks and the city's architecture.
Tip: On NYE it closes to the public at 11 pm except for ticketed parties; walk it on Dec 30 or the afternoon of the 31st instead.
Photo: ajay_suresh · CC BY 2.0
Navy Pier New Year's Eve Fireworks
The Loop & Chicago River · On our Chicago New Year's Eve route
Free midnight fireworks over Lake Michigan, visible from inside and outside along the mile-long pier; held in 2024 and 2025.
Tip: The east end gets crowded early; Milton Lee Olive Park just north of the pier has a quieter lakefront view.
Photo: edward stojakovic · CC BY 2.0
Lincoln Park 2 picks
Lincoln Park Conservatory
Lincoln Park · On our Chicago New Year's Eve route
Free 1890s glasshouse full of palms, ferns and orchids; warm and green on a grey January day.
Tip: Holiday hours vary; confirm Jan 1 opening before you walk over.
Photo: Ben Schumin · CC BY-SA 2.0
Lincoln Park Zoo
Lincoln Park · On our Chicago New Year's Eve route
Free zoo open every day of the year, with lions, gorillas and polar bears a few minutes from the lake.
Tip: ZooLights typically runs into the first days of January; check dates if you want the evening light show.
Photo: Kenneth C. Zirkel · CC BY-SA 4.0
How we picked these
Every entry is a stop on at least one of TripsCircle's hand-curated routes, chosen by our route editors, who wrote the reason to go shown with each place. These are our curated picks, not a scored ranking: we haven't rated or reviewed them against each other. The list is grouped by destination, and within each destination places that appear on more routes come first.
Prices ($ to $$$$) and visit lengths are rough guides from our route notes, not quotes. Check opening hours before you go.
About this list
How did you choose the things to do in Illinois?
Each one is a stop on a TripsCircle route that our editors built by hand, and each comes with a written reason to go. This page shows all 16 of them. They are curated picks, not a ranked score.
Which part of Illinois has the most things to do on this list?
Chicago has the most (10 of 16), followed by The Loop & Chicago River (4) and Lincoln Park (2).
Are any of these free?
8 picks on this list are marked free in our route notes: Art on the Mart, Lincoln Park Conservatory, Chicago River NYE Fireworks, Lincoln Park Zoo, Chicago Riverwalk, and more. Check ahead, since parking or special exhibits can cost extra.
More lists for Illinois
Top things to do nearby
Destinations on this list
- Chicago 10 on this list
- The Loop & Chicago River 4 on this list
- Lincoln Park 2 on this list
Turn this list into a plan
Open a curated route in TripsCircle, add the spots your crew wants, vote with polls and keep everyone on one shared itinerary.