MapVivid
Skydeck Chicago at Willis Tower and around
A day in Chicago · 9:30–17:00 · 6 stops
Open it on your phone:
mapvivid.com/chicago/itineraries/skydeck-chicago-at-willis-tower-and-aroundA walking day around Skydeck Chicago at Willis Tower, Art Institute of Chicago and Chicago Cultural Center, with a lunch break nearby and Buckingham Fountain to end the day.
Every stop on Google Maps: open the list
Morning
9:301Skydeck Chicago at Willis Tower ↗1 hGo early
Glass-floored ledge 103 floors up.
- Book timed tickets
- Clear days are best
↓ 18 min walk
10:452Art Institute of Chicago ↗1 h 30 min
World-class museum with Impressionist and American art.
- Free for Illinois residents on select days
- Enter at Modern Wing for shorter lines
↓ 8 min walk
12:303Chicago Cultural Center ↗30 min
Free landmark with the worlds largest Tiffany glass dome.
- Free admission
- Check free concerts
↓ 3 min walk
13:004Reflective stainless steel sculpture in Millennium Park.
- Go at sunrise for empty photos
- Free to visit
Lunch
14:00Lunch break nearby · Find restaurants nearby on Google Maps ↗
↓ 4 min walk
Afternoon
15:155↓ 13 min walk
16:006Grand 1927 fountain in Grant Park.
- Water shows run April to October
- Best at dusk when lit
Good to know. Times are a guide for an unhurried pace. Check opening days 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.
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.
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.
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.
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.
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.
Planned with MapVivid. Opening hours change, so check each place before you go. This day, with the map: mapvivid.com/chicago/itineraries/skydeck-chicago-at-willis-tower-and-around
Day 1 of 29:30–17:006 stops
Skydeck Chicago at Willis Tower and around
A walking day around Skydeck Chicago at Willis Tower, Art Institute of Chicago and Chicago Cultural Center, with a lunch break nearby and Buckingham Fountain to end the day.
Opens Google Maps with every stop of the day, ready to save to your own list.
Morning
109:30 · 1 hGlass-floored ledge 103 floors up.
- Tip: Go early
2 tips
- Book timed tickets
- Clear days are best
📷 Photos
18 min walk
210:45 · 1 h 30 minWorld-class museum with Impressionist and American art.
3 tips
- Free for Illinois residents on select days
- Enter at Modern Wing for shorter lines
- Find the lion statues out front
📷 Photos
8 min walk
312:30 · 30 minFree landmark with the worlds largest Tiffany glass dome.
3 tips
- Free admission
- Check free concerts
- Look up at the Tiffany dome
📷 Photos
3 min walk
413:00 · 1 hReflective stainless steel sculpture in Millennium Park.
3 tips
- Go at sunrise for empty photos
- Free to visit
- Walk underneath for the omphalos
📷 Photos
Lunch
Lunch break nearby · 14:00
Find restaurants nearby on Google Maps4 min walk
Afternoon
515:15 · 30 minNaturalistic perennial garden in Millennium Park.
3 tips
- Best in summer bloom
- Free entry
- Quiet escape from the crowds
📷 Photos
13 min walk
616:00 · 1 hGrand 1927 fountain in Grant Park.
3 tips
- Water shows run April to October
- Best at dusk when lit
- Free to visit
📷 Photos
Take this day with you
Add the stops to your calendar
Times are local time in Chicago. Apple Calendar adds every stop at once (Outlook too). Google Calendar adds one event per link.
Times are a guide for an unhurried pace. Check opening days before you go.