Looking for the best things to do in Chicago? Chicago is a city of bold architecture, a sparkling lakefront, world-class museums and deep-dish pizza, with neighbourhoods full of blues clubs and restaurants. This list mixes famous landmarks with local favourites and easy day trips, with practical tips on timing, tickets and costs for American travellers.
Best things to do in Chicago
1. Chicago Architecture Center river cruise
The best way to see the city’s skyscrapers. Wear comfortable shoes; you will walk more than you expect.
2. Millennium Park and Cloud Gate
The reflective “Bean” and free summer concerts. Book tickets online to skip the line.
3. Art Institute of Chicago
Masterpieces including Seurat and Hopper. Weekdays are much quieter than weekends.
4. Navy Pier
Lakefront attractions and fireworks in summer. Weekdays are much quieter than weekends.
5. Skydeck at Willis Tower
Glass ledges 1,353 feet up. Weekdays are much quieter than weekends.
6. Lincoln Park Zoo
A free zoo near the lake. It is great value for families.
Travel tech we recommend
- Cameras for landscape photography BuyrSkip
Canyons, coastlines and city skylines reward a camera with great dynamic range. - Waterproof action cameras BuyrSkip
Film snorkelling, ziplines and mountain biking hands-free.
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7. Museum Campus
The Field Museum, Shedd Aquarium and Adler Planetarium. Check opening hours before you go, as they change seasonally.
8. Wrigley Field
The historic home of the Cubs. Book tickets online to skip the line.
9. River cruises
One of the most popular ways to experience Chicago; ask your hotel or a local outfitter for current options and prices. Wear comfortable shoes; you will walk more than you expect.
10. Blues and jazz clubs
One of the most popular ways to experience Chicago; ask your hotel or a local outfitter for current options and prices. Check opening hours before you go, as they change seasonally.
11. Lakefront biking
One of the most popular ways to experience Chicago; ask your hotel or a local outfitter for current options and prices. Bring a refillable water bottle.
12. Improv comedy
One of the most popular ways to experience Chicago; ask your hotel or a local outfitter for current options and prices. It is great value for families.
13. Food tours
One of the most popular ways to experience Chicago; ask your hotel or a local outfitter for current options and prices. Check opening hours before you go, as they change seasonally.
14. Take a day trip to New York City
New York City packs world-famous museums, Broadway theatres, iconic skyline views and food from every corner of the globe into five boroughs. Read our New York City travel guide. It is great value for families.
15. Eat your way through the local food scene
Try deep-dish pizza, Chicago-style hot dogs, Italian beef and Garrett popcorn. Food tours are a fun way to sample several places in one afternoon. Wear comfortable shoes; you will walk more than you expect.
When to go
The best time to visit is May to October.
| Season | Months | What to expect |
|---|---|---|
| Spring | March–May | Changeable, 40–70°F. |
| Summer | June–August | Warm to hot, festival season. |
| Fall | September–November | Crisp, colourful and pleasant. |
| Winter | December–February | Very cold, often below freezing, with wind and snow. |
Where to stay
- The Loop: Central and close to museums.
- River North: Restaurants and nightlife.
- Magnificent Mile: Shopping and classic hotels.
- West Loop: Top restaurants.
| Style | Typical price per night | What you get |
|---|---|---|
| Budget | $110–170 | Motels, hostels, simple inns and campground cabins |
| Mid-range | $180–300 | Comfortable hotels and B&Bs, often with breakfast |
| Luxury | $350–700 | Resorts, historic hotels and boutique properties |
For more detail, read our Chicago travel guide.
Tips for visitors
- Winters are bitterly cold; summer is festival season.
- Use the “L” trains from both airports.
- Book the architecture cruise in advance in summer.
Common mistakes to avoid
- Trying to cover every neighbourhood in a day: cluster sights by area instead.
- Renting a car you will barely use and paying high overnight parking fees.
- Eating only in the main tourist zone, where prices are higher and quality lower.
- Skipping reservations for popular restaurants, tours and observation decks on weekends.
- Underestimating walking distances: bring comfortable shoes.
Sample 3-day budget for two
| Item | Mid-range estimate |
|---|---|
| Hotel (3 nights) | $540–$900 |
| Food and drink | $540–$864 |
| Activities and entry fees | $140–$280 |
| Local transport or car | $180–$270 |
| Total | $1,400–$2,314 |
Estimates exclude flights and assume a mid-range hotel; travelling in shoulder season can cut accommodation costs by a third or more.
What to pack for Chicago
- Comfortable walking shoes
- A light layer for air-conditioned interiors
- A compact umbrella
- A crossbody bag or small backpack
- A portable charger
- A smart outfit for nicer restaurants
For a complete checklist, see our road trip packing list.
Planning tips for your trip
- ID for flights: Domestic flights require a REAL ID-compliant licence or another accepted ID such as a passport. See our guide to REAL ID and TSA rules.
- Money: Sales tax is added at the register and varies by state and city; tipping 18–20% at sit-down restaurants is expected.
- Insurance: Your health plan may have limited out-of-network cover in another state, and trip-cancellation cover is worth having for expensive bookings, especially in hurricane season.
- Driving: Most visitors drive; rental cars are widely available, and a US licence is all you need. Gas prices vary widely by state; California and Hawaii are usually the most expensive.
- Saving money: our budget vacation and cheapest places to travel guides have dozens of practical ideas.
What a trip costs
Typical spending per person per day, excluding flights:
| Travel style | Per person per day | Covers |
|---|---|---|
| Budget | $120–$180 | motel or hostel, casual meals, self-drive or transit |
| Mid-range | $250–$400 | good hotel, sit-down meals, some tours |
| Luxury | $600–$1,200 | resort or boutique hotel, fine dining, private tours |
Prices rise in peak season and on holiday weekends, and fall sharply in the shoulder seasons.
Responsible travel tips
Popular places are under pressure from crowds. Visit on weekdays or in shoulder seasons, carpool or use shuttles, refill a reusable water bottle, and buy from local businesses. Respect Indigenous lands and cultural sites, follow posted closures, and keep a safe distance from wildlife.
Safety basics
Carry water and layers on outdoor outings, check weather and road conditions before long drives, and tell someone your plans in remote areas, where mobile coverage can be patchy. In cities, use normal precautions with valuables at night. The emergency number is 911.
Pack smarter
- Best travel backpacks BuyrSkip
A 30–40 litre backpack handles a long weekend and fits under most airline seats. - Best phones and wearables for travel Buyzello
Phones with great cameras and wearables that track your hikes. - Top-rated wireless earbuds VerdictFox
Compact earbuds for flights, trains and long drives.
Partner links: these go to our sister review sites, which may earn a commission at no extra cost to you.
Frequently asked questions
What is the number one thing to do in Chicago?
For most first-time visitors it is Chicago Architecture Center river cruise: the best way to see the city’s skyscrapers.
How many days do you need in Chicago?
Plan 3 days to cover the highlights at a relaxed pace.
What is the best time to visit Chicago?
May to October.
Is Chicago good for families?
Yes. Many of the top attractions suit children, and Chicago is popular with architecture fans, foodies, families and culture lovers.
What should I eat in Chicago?
Try deep-dish pizza, Chicago-style hot dogs, Italian beef and Garrett popcorn.
Plan the rest of your trip
- Chicago Travel Guide: Architecture, Food and Neighbourhoods
- Chicago 3-Day Itinerary: Architecture, Museums and Deep Dish
- New York City Travel Guide: Neighbourhoods, Top Sights and Tips