TripSmithChicago
A curated guide to Chicago, United States: 8 top sights, 8 standout places to eat, where to stay, and a sample itinerary.
What to see
- Chicago Riverwalk 4.8★ (22,000 reviews) · Tourist attraction
- Millennium Park 4.8★ (92,000 reviews) · Tourist attraction
- The Art Institute of Chicago 4.8★ (38,000 reviews) · Museum
- 875 North Michigan Avenue 4.7★ (20,000 reviews) · Tourist attraction
- Cloud Gate 4.7★ (39,000 reviews) · Tourist attraction
- Grant Park 4.7★ (21,000 reviews) · Tourist attraction
- Crown Fountain 4.7★ (5,500 reviews) · Tourist attraction
- Field Museum 4.7★ (31,000 reviews) · Natural history museum
Where to eat
- Alla Vita 4.8★ (5,100 reviews) · Restaurant
- Quartino Ristorante 4.7★ (16,000 reviews) · Italian
- The Wormhole Coffee 4.6★ (2,100 reviews) · Coffee shop
- Sawada Coffee 4.6★ (2,200 reviews) · Coffee shop
- Goddess and the Baker, 33 S Wabash-Millennium Park 4.3★ (2,900 reviews) · Cafe
- Hexe Coffee Co. 4.8★ (1,000 reviews) · Cafe
- Ground Up Coffee & Bites 4.6★ (778 reviews) · Coffee shop
- Kapéj Coffee Roasters 4.7★ (660 reviews) · Coffee shop
Where to drink
- Gus' Sip & Dip 4.9★ (2,900 reviews) · Bar
- Three Dots and a Dash 4.6★ (8,500 reviews) · Cocktail bar
- Howl at the Moon Chicago 4.4★ (3,800 reviews) · Bar
- Brando's Speakeasy 4.3★ (2,100 reviews) · Karaoke bar
- LH Rooftop 4.2★ (3,700 reviews) · Bar
A sample 3-day shape
Day 1
- Morning: Chicago Riverwalk
- Afternoon: 875 North Michigan Avenue
- Dinner: Alla Vita
- Nightcap: Gus' Sip & Dip
Day 2
- Morning: Millennium Park
- Afternoon: Cloud Gate
- Dinner: Quartino Ristorante
- Nightcap: Three Dots and a Dash
Day 3
- Morning: The Art Institute of Chicago
- Afternoon: Grant Park
- Dinner: The Wormhole Coffee
- Nightcap: Howl at the Moon Chicago
This is a starting shape — plan your own Chicago trip →
Frequently asked
How many days do you need in Chicago?
With 20 notable sights and 9 standout eateries, 2–4 days covers the essentials at a relaxed pace.