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35 hand-picked places in 10 lists. Tick the categories you want to see on the map.

Only have a day? See 2 ready-made day plans ↓
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Tips

10 places on the map

Free things to do

  1. 1

    Reflective stainless steel sculpture in Millennium Park.

    3 tips
    • Go at sunrise for empty photos
    • Free to visit
    • Walk underneath for the omphalos
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  2. 2

    Downtown park with gardens, lawns and public art beside Michigan Avenue.

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  3. 3

    Naturalistic perennial garden in Millennium Park.

    3 tips
    • Best in summer bloom
    • Free entry
    • Quiet escape from the crowds
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  4. 4

    Grand 1927 fountain in Grant Park.

    3 tips
    • Water shows run April to October
    • Best at dusk when lit
    • Free to visit
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  5. 5

    Pedestrian path along the river with cafes and views.

    • Tip: Sunset
    3 tips
    • Take an architecture boat cruise
    • Sunset drinks on the water
    • Walk from Lake Street to Michigan Avenue
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  6. 6

    Free landmark with the worlds largest Tiffany glass dome.

    3 tips
    • Free admission
    • Check free concerts
    • Look up at the Tiffany dome
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  7. 7

    Free zoo in Lincoln Park with city views.

    3 tips
    • Admission is free
    • Visit the Regenstein African Journey
    • Walk to the lakefront after
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  8. 8

    Lakefront pier with Ferris wheel, shops and boat tours.

    • Tip: Sunset
    3 tips
    • Fireworks on summer weekends
    • Ride the Centennial Wheel at sunset
    • Walk or take the free trolley
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  9. 9

    City beach with a skyline backdrop.

    3 tips
    • Lifeguards in summer
    • Great sunrise photos
    • Rent a bike on the lakefront path
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  10. 10

    Upscale shopping stretch of North Michigan Avenue.

    3 tips
    • Look for the historic Water Tower
    • See the holiday lights in winter
    • Visit the 360 CHICAGO observatory
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Before you go: Chicago tips

Transportation

  • Ride the L from the airports: the Blue Line runs from O'Hare and the Orange Line from Midway into the Loop; tap a Ventra card, the Ventra app or a contactless bank card.
  • Take the Chicago Water Taxi: in warmer months these yellow boats link the Ogilvie Transportation Center, Michigan Avenue and Chinatown along the river, a fun alternative to the bus.
  • Cycle the Lakefront Trail with Divvy: grab a Divvy bike or e-bike and ride the 18-mile Lakefront Trail past beaches, Navy Pier and Museum Campus with skyline views.

Security

  • Guard your phone on the L: phone snatching near train doors happens, so keep devices away from the doorway, ride in occupied cars at night and stay alert on platforms.
  • Respect Lake Michigan waves: strong currents near piers and breakwaters can be deadly, so swim only at lifeguarded beaches and stay off rock edges on windy days.
  • Avoid leaving bags in cars: car break-ins are common, so take luggage and valuables with you rather than leaving them visible when parked in River North or near beaches.

Saving

  • Buy a Ventra day pass: unlimited 1, 3 and 7 day passes cover CTA trains and buses, and pay off quickly if you hop between neighbourhoods like Wicker Park and Hyde Park.
  • Enjoy free summer concerts: the Grant Park Music Festival and many events at Millennium Park's Jay Pritzker Pavilion are free; bring a picnic blanket to the Great Lawn.
  • Book a free Chicago Greeter tour: volunteers lead free neighbourhood walks in places like Pilsen and Chinatown; request a tour online a couple of weeks ahead.

Weather/Clothing

  • Dress for wind chill in winter: from December to February icy winds off the lake make it feel far colder than the thermometer, so pack a long parka, hat, gloves and scarf.
  • Plan for humid summers: July and August can be hot and sticky with thunderstorms, so bring light breathable clothes and a compact umbrella for sudden downpours.
  • Layer up near the lake: in spring and fall it is often cooler by the lake than inland, so carry a jacket for evenings at Navy Pier or along the Riverwalk.

Cultural

  • Eat like a local: try an Italian beef dipped and hot, a Chicago dog with no ketchup, and tavern-style thin crust pizza cut in squares, which locals eat more than deep dish.
  • Hear live blues and jazz: catch blues at clubs like Kingston Mines or Buddy Guy's Legends, or jazz at the Green Mill in Uptown, part of Chicago's rich music heritage.
  • Tip properly: servers and bartenders expect around 18 to 20 percent, and a dollar or two per drink at the bar is normal; tipping rideshare drivers is also common.

Local Hacks

  • Use the Pedway in winter: this underground network links Loop buildings and stations, so you can walk between Millennium Station, Macy's and City Hall out of the cold.
  • Take the architecture river cruise: the Chicago Architecture Center's boat tour explains the skyscrapers from the river; daytime trips give the best photos of the buildings.
  • Explore beyond the Loop: walk Pilsen's murals and taquerias, see Wicker Park's indie shops, or visit Hyde Park's Museum of Science and Industry and the University of Chicago.

1-day itineraries in Chicago

Only have a day? Each one keeps you in one area, from morning to late afternoon, with lunch nearby.

Day 1 of 2

Skydeck Chicago at Willis Tower and around

🕘 9:30–17:00📍 6 stops

  1. 1Skydeck Chicago at Willis Tower
  2. 2Art Institute of Chicago
  3. 3Chicago Cultural Center
  4. 4Cloud Gate (The Bean)
  5. 5Lurie Garden
  6. and 1 more
See the day →

Day 2 of 2

Magnificent Mile and around

🕘 9:30–17:30📍 5 stops

  1. 1Magnificent Mile
  2. 2Museum of Contemporary Art Chicago
  3. 3Chicago Riverwalk
  4. 4Chicago Architecture Center
  5. 5Navy Pier
See the day →

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