# 3 Days In Chicago: Cloud Gate, Willis Tower & Art Institute

> A city break in Chicago for four. You'll see the Willis Tower Skydeck, Cloud Gate, the Art Institute of Chicago and Kingston Mines. You stay at The Robey.

- Destination: Chicago, United States
- Starts in: New York City, United States
- Region: [North America](https://travelyfe.com/explore/north-america)
- Length: 3 days, 22 stops
- Author: [Travelyfe](https://travelyfe.com/@travelyfe)
- Published: 16 Aug 2026
- Updated: 5 Oct 2026
- Web page: https://travelyfe.com/itineraries/50000000-0000-4000-8000-000000000060

## Day 1

1. **Breakfast At Dove's Luncheonette** (08:00, Café, 1 h) — 1545 N Damen Avenue, Chicago, IL 60622, United States
   - Next: 20 min transit
2. **Chicago Riverwalk** (09:45, Activity, 1 h 5 min) — Chicago Riverwalk, Chicago, IL 60601, United States
   - Next: 17 min transit
3. **Willis Tower Skydeck** (11:15, Viewpoint, 1 h 15 min) — 233 S Wacker Drive, Chicago, IL 60606, United States
   - Next: 5 min walk
4. **The Rookery Light Court** (12:45, Landmark, 45 min) — 209 S LaSalle Street, Chicago, IL 60604, United States
   - Next: 3 min walk
5. **Lunch At Revival Food Hall** (13:45, Restaurant, 1 h) — 125 S Clark Street, Chicago, IL 60603, United States
   - Next: 13 min walk
6. **Millennium Park And Cloud Gate** (15:05, Landmark, 1 h 15 min) — 201 E Randolph Street, Chicago, IL 60602, United States
   - Next: 5 min walk
7. **Art Institute Of Chicago** (16:35, Activity, 2 h 30 min) — 111 S Michigan Avenue, Chicago, IL 60603, United States
   - Next: 16 min walk
8. **Dinner At The Purple Pig** (19:35, Restaurant, 1 h 45 min) — 444 N Michigan Avenue, Chicago, IL 60611, United States

## Day 2

1. **Breakfast At Bru** (08:15, Café, 45 min) — 1562 N Milwaukee Ave, Chicago, IL  60622, United States
   - Next: 35 min transit
2. **Field Museum** (09:50, Activity, 2 h 30 min) — 1400 S Lake Shore Drive, Chicago, IL 60605, United States
   - Next: 16 min walk
3. **Lunch At Eleven City Diner** (12:45, Restaurant, 1 h) — 1112 S Wabash Avenue, Chicago, IL 60605, United States
   - Next: 18 min walk
4. **Shedd Aquarium** (14:10, Museum, 1 h 30 min) — 1200 S Lake Shore Drive, Chicago, IL 60605, United States
   - Next: 10 min walk
5. **Adler Planetarium Point** (16:00, Viewpoint, 30 min) — 1300 S Lake Shore Drive, Chicago, IL 60605, United States
   - Next: 49 min transit
6. **North Avenue Beach** (17:25, Beach, 1 h 30 min) — 1601 N Jean-Baptiste Pointe DuSable Lake Shore Drive, Chicago, IL 60611, United States
   - Next: 47 min transit
7. **Dinner At Girl & The Goat** (19:55, Restaurant, 2 h) — 809 W Randolph Street, Chicago, IL 60607, United States

## Day 3

1. **Breakfast At Mindy’s Bakery** (08:15, Café, 45 min) — 1623 N Milwaukee Ave, Chicago, IL  60647, United States
   - Next: 23 min transit
2. **606 Bloomingdale Trail** (09:40, Activity, 1 h 5 min) — 1805 N Ridgeway Avenue, Chicago, IL 60647, United States
   - Next: 29 min transit
3. **Wicker Park Milwaukee Avenue** (11:20, Shopping, 1 h 25 min) — Milwaukee Avenue, Chicago, IL 60622, United States
   - Next: 24 min transit
4. **Lunch At Lou Malnati's Pizzeria** (13:15, Restaurant, 1 h 30 min) — 1520 N Wells Street, Chicago, IL 60610, United States
   - Next: 5 min walk
5. **Chicago History Museum** (15:00, Museum, 1 h 45 min) — 1601 N Clark Street, Chicago, IL 60614, United States
   - Next: 38 min transit
6. **Dinner At The Publican** (18:45, Restaurant, 1 h 50 min) — 837 W Fulton Market, Chicago, IL 60607, United States
   - Next: 31 min transit
7. **Kingston Mines** (21:15, Evening Out, 1 h 45 min) — 2548 N Halsted Street, Chicago, IL 60614, United States

## Where To Stay

- The Robey — 2018 W North Avenue, Chicago, IL 60647, United States

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