# 4 Days In Chicago: Willis Tower, Riverwalk & Wrigley Field

> A Transformers style city break in Chicago for four friends. You'll see Willis Tower, Millennium Park, the Chicago Riverwalk, Navy Pier and Wrigley Field. You stay at Hotel Chicago Downtown, Autograph Collection.

- Destination: Chicago, United States
- Starts in: Toronto, Canada
- Region: [North America](https://travelyfe.com/explore/north-america)
- Length: 4 days, 25 stops
- Author: [Travelyfe](https://travelyfe.com/@travelyfe)
- Published: 30 Sep 2026
- Updated: 5 Oct 2026
- Web page: https://travelyfe.com/itineraries/78510f0e-0855-4f3e-b2ba-b2998a7ae254

## Day 1

1. **Lunch At Portillo's** (12:30, Restaurant, 1 h) — 88 E Wacker Pl, Chicago, IL  60601, United States
   - Next: 9 min walk
2. **Millennium Park** (13:45, Landmark, 1 h 15 min) — 201 E Randolph St, Chicago, IL  60601, United States
   - Next: 6 min walk
3. **Art Institute of Chicago** (15:15, Museum, 2 h) — 111 S Michigan Ave, Chicago, IL 60603, United States
   - Next: 13 min walk
4. **Chicago Architecture Center** (17:30, Activity, 1 h 30 min) — 111 E Wacker Dr, Chicago, IL  60601, United States
   - Next: 5 min walk
5. **Dinner At Lou Malnati's Pizzeria** (19:30, Restaurant, 1 h 30 min) — The Wrigley Building, 422 N Michigan Ave, Chicago, IL  60611, United States

## Day 2

1. **Breakfast At Wildberry Pancakes and Cafe** (08:30, Café, 1 h) — 130 E Randolph St, Chicago, IL  60601, United States
   - Next: 13 min transit
2. **Willis Tower** (10:00, Activity, 1 h 30 min) — 233 S Wacker Dr, Chicago, IL  60606-7147, United States
   - Next: 2 min walk
3. **S Lower Wacker Dr** (11:45, Landmark, 30 min) — S Lower Wacker Dr, Chicago, IL  60606, United States
   - Next: 16 min walk
4. **Lunch At Billy Goat Tavern** (12:45, Restaurant, 1 h) — Merchandise Mart Station, 300 N Wells St, Chicago, IL  60654, United States
   - Next: 15 min walk
5. **The Wrigley Building** (14:15, Landmark, 30 min) — 400-410 N Michigan Ave, Chicago, IL 60611, United States
   - Next: 5 min walk
6. **Chicago Riverwalk** (15:00, Nature, 1 h 15 min) — 2 N La Salle St, Floor 2, Chicago, IL 60602, United States
   - Next: 13 min transit
7. **Navy Pier** (16:45, Activity, 2 h) — 600 E Grand Ave, Chicago, IL  60611, United States
   - Next: 38 min transit
8. **Dinner At Girl & the Goat** (19:45, Restaurant, 1 h 30 min) — 809 W Randolph St, Chicago, IL  60607, United States

## Day 3

1. **Breakfast At Do-Rite Donuts & Chicken** (08:30, Café, 45 min) — Northwestern University, 233 E Erie St, Chicago, IL  60611, United States
   - Next: 11 min walk
2. **360 Chicago** (09:30, Viewpoint, 1 h 15 min) — 875 N Michigan Ave, FL 94, Chicago, IL 60611, United States
   - Next: 3 min walk
3. **Magnificent Mile** (11:00, Shopping, 1 h 15 min) — Magnificent Mile, Chicago, IL, United States
   - Next: 12 min transit
4. **Lunch At Giordano's** (12:45, Restaurant, 1 h 15 min) — Millennium Station, 122 E Randolph St, Chicago, IL  60601, United States
   - Next: 25 min transit
5. **Shedd Aquarium** (14:30, Activity, 2 h) — 1200 S DuSable Lake Shore Dr, Chicago, IL 60605, United States
   - Next: 7 min walk
6. **Field Museum** (16:45, Museum, 1 h 30 min) — 1400 S DuSable Lake Shore Dr, Chicago, IL  60605, United States
   - Next: 32 min transit
7. **Dinner At Au Cheval** (19:00, Restaurant, 1 h 30 min) — 800 W Randolph St, Chicago, IL  60607, United States
   - Next: 16 min drive
8. **Kingston Mines** (21:00, Evening Out, 1 h 30 min) — 2548 N Halsted St, Chicago, IL 60614, United States

## Day 4

1. **Breakfast At Lou Mitchell's** (09:00, Restaurant, 1 h) — 565 W Jackson Blvd, Chicago, IL  60661, United States
   - Next: 35 min transit
2. **Wrigley Field** (10:45, Activity, 1 h 30 min) — 1060 W Addison St, Chicago, IL  60613, United States
   - Next: 9 min drive
3. **Lunch At Pequod's Pizza** (12:45, Restaurant, 1 h 15 min) — 2207 N Clybourn Ave, Chicago, IL  60614, United States
   - Next: 14 min drive
4. **Lincoln Park Zoo** (14:15, Activity, 1 h 30 min) — 2400 N. Cannon Drive, Chicago, IL 60614, United States

## Where To Stay

- Hotel Chicago Downtown, Autograph Collection — 333 N Dearborn St, Chicago, IL  60654, United States

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