Chicago deserves its reputation as one of America’s greatest cities. World-class museums, stunning architecture, incredible food, and a lakefront that rivals any coastline make it a destination worth visiting.
This guide answers the key question: what should I know before visiting Chicago? Whether you’re a seasoned traveler or planning your first big city trip, you’ll find everything you need to make vacationing in Chicago memorable.
Vacationing in Chicago
1. When to Visit Chicago: Best and Worst Times
Timing makes or breaks a Chicago vacation. The city experiences four distinct seasons, and each brings different experiences and challenges.
Best Times for Vacationing in Chicago
Late spring (May to early June):
- Average temperatures: 60 to 75°F
- Lower hotel rates than peak summer
- Fewer crowds at major attractions
- Gardens and parks in full bloom
- Outdoor festivals begin
Early fall (September to October):
- Average temperatures: 55 to 70°F
- Beautiful autumn colors in parks
- Chicago Marathon and fall festivals
- Hotel rates drop after Labor Day
- Comfortable weather for walking tours
Summer (July to August):
- Peak tourist season
- Average temperatures: 75 to 85°F
- Beach weather and outdoor activities
- Major festivals and events
- Expect crowds and higher prices
Worst Times to Visit
Winter (December to February):
- Average temperatures: 15 to 35°F
- Wind chill can reach -20°F or lower
- Many outdoor attractions closed
- Shorter daylight hours (darkness by 4:30 PM)
- Risk of flight delays due to snow
Late November:
- Thanksgiving week brings massive crowds
- Hotel prices spike 40% to 60%
- Restaurants require reservations weeks ahead
- Magnificent Mile shopping areas overcrowded
Month-by-Month Breakdown
January to February: coldest months, hotel deals available, indoor attractions only
March to April: unpredictable weather, mix of snow and rain, moderate crowds
May: ideal weather begins, reasonable prices, festival season starts
June: warm and pleasant, prices increase, summer crowds arrive
July to August: peak season, highest prices, most crowded, best weather
September: perfect weather, fewer crowds, excellent value
October: beautiful fall colors, comfortable temperatures, good prices
November: cold arrives, Thanksgiving crowds, variable weather
December: holiday events, very cold, expensive during holidays
2. Cloud Gate at Millennium Park: Chicago’s Number One Tourist Attraction
Cloud Gate, known as “The Bean,” is Chicago’s most photographed landmark. Over 12 million people visit annually, making it the city’s top attraction.
What Makes Cloud Gate Special
British artist Anish Kapoor designed this 110-ton stainless steel sculpture. Its mirror-like surface reflects Chicago’s skyline and the faces of visitors standing beneath it.
The sculpture measures:
- 66 feet long
- 33 feet high
- Made from 168 welded stainless steel plates
Best Times to Visit Cloud Gate
Early morning (6 AM to 8 AM):
- Almost no crowds
- Best photos without people in the background
- Soft morning light
- Free and easy access
Weekdays in shoulder season:
- Moderate crowds
- Better than weekends
- Still manageable for photos
Avoid these times:
- Weekends from 10 AM to 5 PM (packed)
- Summer afternoons (wait times for photos)
- After 7 PM in winter (too dark, sculpture hard to see)
Photography Tips
Walk underneath the sculpture for distorted reflections. Stand at the center point under the arch for the most dramatic effect.
Use wide-angle lens or phone panorama mode to capture the full sculpture.
Visit twice: once during day for skyline reflections, once at sunset for golden hour photos.
What Else to See at Millennium Park
Crown Fountain: two 50-foot glass towers with LED faces that spit water
Lurie Garden: 5-acre garden with native plants and walking paths
Jay Pritzker Pavilion: Frank Gehry designed outdoor concert venue
BP Bridge: winding pedestrian bridge with skyline views
Budget 2 to 3 hours to explore the entire park properly.
3. Must-See Museums and Cultural Attractions
Chicago houses world-class museums. Many cluster near Grant Park, making museum hopping easy.
The Art Institute of Chicago
The Art Institute of Chicago is one of the world’s oldest and largest art museums. The collection includes:
- 300,000 works of art
- Impressionist and Post-Impressionist masterpieces
- American Gothic by Grant Wood
- A Sunday on La Grande Jatte by Georges Seurat
Admission: 32 dollars for adults Time needed: 3 to 4 hours minimum Best day: weekday mornings
Illinois residents get free admission on specific days. Check the website before visiting.
Field Museum of Natural History
Home to Sue, the largest and most complete T-Rex skeleton ever discovered.
Other highlights:
- Ancient Egypt collection (23 mummies)
- Evolving Planet exhibit (4 billion years of life)
- Underground Adventure (shrink to bug size)
- Grainger Hall of Gems (precious stones and jewelry)
Admission: 29 dollars for basic, 39 dollars for all-access Time needed: 4 to 5 hours Best day: Tuesday or Wednesday
Museum of Science and Industry
The largest science museum in the Western Hemisphere. Interactive exhibits make it perfect for families.
Top exhibits:
- U-505 German submarine captured in WWII
- Science Storms (tornadoes, avalanches, fire)
- Coal Mine (descend into a working mine replica)
- Yesterday’s Main Street (1910s Chicago neighborhood)
Admission: 25 dollars for adults Time needed: Full day (4 to 6 hours) Best day: weekday mornings in off-season
Shedd Aquarium
One of the world’s largest indoor aquariums. Houses 32,000 animals.
Key attractions:
- Caribbean Reef (sharks, sea turtles, stingrays)
- Amazon Rising (anacondas, piranhas, caimans)
- Wild Reef (sharks walk beneath you in tunnel)
- Dolphin shows (additional cost)
Admission: 40 dollars for standard, 50 dollars with shows Time needed: 2 to 3 hours Best time: weekday afternoons
Money-Saving Museum Tips
Chicago CityPASS: 109 dollars for adults, includes 5 attractions, saves 53% off regular admission
Go Chicago Pass: unlimited attractions for 1 to 5 days, starting at 109 dollars
Free museum days: many museums offer free days for Illinois residents
Visit in winter: some museums reduce prices November through February
4. Architectural Tours and Skyline Views
Chicago invented the skyscraper. The city’s architecture tells the story of American urban development.
Chicago Architecture River Cruise
The single best way to understand Chicago’s architecture. Boats cruise along the Chicago River while guides explain the buildings.
Details:
- Duration: 75 to 90 minutes
- Cost: 45 to 55 dollars per person
- Frequency: departures every 30 to 60 minutes
- Season: April through November
Book tickets 2 to 3 days in advance for preferred times. Morning and late afternoon cruises offer the best light for photos.
Major tour operators:
- Chicago Architecture Foundation (most detailed commentary)
- Wendella Boats (longest running company)
- Shoreline Sightseeing (budget friendly option)
360 Chicago Observation Deck
Located on the 94th floor of the John Hancock Building. Height: 1,000 feet above street level.
Why visit:
- Less crowded than Willis Tower
- Better views of Lake Michigan
- TILT experience (tilted windows over Michigan Avenue)
- Cheaper admission than Willis Tower
Admission: 30 dollars for adults, 39 dollars with TILT Hours: 9 AM to 11 PM daily Best time: sunset (arrive 45 minutes before sunset)
Willis Tower Skydeck
The famous glass ledges extending from the 103rd floor. Height: 1,353 feet.
What to expect:
- Long wait times (30 to 90 minutes in peak season)
- Four glass boxes jutting out from the building
- Views spanning four states on clear days
- Crowds and line management challenges
Admission: 35 to 45 dollars depending on time Strategy: buy timed tickets online, visit early morning or after 6 PM
Walking Architecture Tours
Chicago Architecture Foundation offers walking tours focused on specific neighborhoods.
Popular tours:
- Historic Skyscrapers (Downtown Loop)
- Modern Architecture (Michigan Avenue)
- Frank Lloyd Wright in Oak Park (suburb)
Cost: 20 to 30 dollars per person Duration: 90 to 120 minutes Booking: reserve online 1 to 2 weeks ahead for popular tours
5. Best Neighborhoods to Explore
Chicago is a city of neighborhoods. Each has distinct character, food, and attractions.
The Loop
Chicago’s downtown center. Home to:
- Millennium Park
- Art Institute
- Theater District
- Willis Tower
- Shopping on State Street
Best for: sightseeing, museums, architecture Walk this area: safe during day, mostly business district
River North
Gallery district turned nightlife hub.
Features:
- 100+ art galleries
- Upscale restaurants
- Trendy bars and clubs
- Easy walking from downtown
Best for: art lovers, nightlife, dining Safety: good in main areas, use caution late night
Lincoln Park
Upscale residential neighborhood along the lake.
Highlights:
- Lincoln Park Zoo (free admission)
- Lincoln Park Conservatory
- Beaches and lakefront trail
- Shopping on Armitage Avenue
Best for: families, outdoor activities, relaxed atmosphere Safety: very safe, family friendly
Wicker Park and Bucktown
Hip neighborhoods with independent shops and restaurants.
Known for:
- Vintage clothing stores
- Live music venues
- Coffee shops and brunch spots
- Street art and murals
Best for: young travelers, music fans, unique shopping Safety: safe in commercial areas, use normal city awareness
Chinatown
Authentic Asian restaurants and shops centered on Cermak Avenue.
Attractions:
- Chinatown Gate
- Ping Tom Memorial Park
- Dim sum restaurants
- Chinese New Year celebrations
Best for: food lovers, cultural experiences Safety: safe during day and evening, stick to main streets
Hyde Park
University of Chicago neighborhood on the South Side.
Must-see:
- Museum of Science and Industry
- University of Chicago campus
- Obama’s former residence (drive by only)
- Jackson Park and lagoons
Best for: museum visitors, architecture fans Safety: stay near campus and museum area, take rideshare at night
6. Chicago Food You Must Try
Chicago food goes beyond deep-dish pizza. The city has distinct culinary traditions worth experiencing.
Deep-Dish Pizza
You’re vacationing in Chicago, so yes, eat the pizza. These places serve the authentic version:
Lou Malnati’s:
- Multiple locations
- Butter crust
- Reservations recommended
- Cost: 30 to 40 dollars for large pizza
Pequod’s:
- Lincoln Park location
- Caramelized crust edge
- Long wait times (arrive when they open)
- Cost: 25 to 35 dollars for large pizza
Giordano’s:
- Stuffed pizza (different from deep-dish)
- Tourist friendly
- Many downtown locations
- Cost: 30 to 40 dollars for large pizza
Order thin-crust too. Chicagoans eat thin-crust more often than deep-dish.
Chicago-Style Hot Dogs
Specific toppings in specific order: yellow mustard, chopped onions, neon green relish, tomato slices, pickle spear, sport peppers, celery salt. Never ketchup.
Best spots:
- Portillo’s (chain, reliable, multiple locations)
- Superdawg (drive-in, 1948, Northwest Side)
- Gene and Jude’s (no seating, near O’Hare)
Cost: 4 to 7 dollars per hot dog
Italian Beef Sandwich
Thin-sliced roast beef on Italian roll, soaked in meat juices. Order it “dipped” (entire sandwich dunked) or “wet” (extra juice).
Classic places:
- Al’s Beef (multiple locations, cash only)
- Portillo’s (tourists love it, locals eat there too)
- Mr. Beef (original, River North)
Cost: 8 to 12 dollars
Where to Eat in Different Neighborhoods
West Loop: restaurant row, upscale dining, chef-driven restaurants
Little Italy: traditional Italian, Taylor Street, family-owned places
Greektown: saganaki (flaming cheese), gyros, Halsted Street
Pilsen: Mexican food, authentic tacos, colorful murals
Devon Avenue: Indian and Pakistani, best samosas, Middle Eastern groceries
7. Getting Around Chicago
Chicago has excellent public transportation. You don’t need a car for most tourist activities.
The L Train System
Eight color-coded lines connect the city. Trains run 24 hours on some lines.
Key tourist lines:
- Red Line: north-south, runs 24 hours, connects most attractions
- Blue Line: to O’Hare Airport, runs 24 hours
- Brown Line: elevated loop around downtown, great views
- Orange Line: to Midway Airport
Cost: 2.50 dollars per ride, 5 dollars for day pass, 20 dollars for 3-day pass
Buy Ventra card at any station. Tap to enter. Keep the card for your entire trip.
Buses
Extensive bus network covers areas trains don’t reach. Route 146 connects Museum Campus to Navy Pier.
Cost: same as trains, transfers free within 2 hours
Google Maps works well for planning bus routes in Chicago.
Rideshare and Taxis
Uber and Lyft operate throughout Chicago. Prices surge during rush hour and major events.
Average costs:
- Loop to Lincoln Park: 12 to 18 dollars
- Loop to Wicker Park: 15 to 22 dollars
- O’Hare to downtown: 35 to 55 dollars (trains cost 5 dollars)
Taxis charge similar rates but harder to find outside downtown.
Biking
Divvy bike share has 600+ stations citywide.
Cost: 3 dollars for 30-minute ride, 15 dollars for day pass
The Lakefront Trail runs 18 miles along Lake Michigan. Separated from traffic, flat terrain, connects beaches and parks.
Best for: warm weather, exploring lakefront neighborhoods
Water Taxis
Water taxis run along the Chicago River connecting downtown points.
Route: Michigan Avenue to Chinatown Cost: 6 to 10 dollars per ride Season: May through September Use: scenic way to reach Museum Campus or Chinatown
8. Where to Stay in Chicago
Location matters in Chicago. Choose your hotel based on what you plan to do.
Best Areas for First-Time Visitors
The Loop and South Loop:
- Walking distance to major attractions
- Connected to L trains
- Hotels: 120 to 300 dollars per night
- Quiet at night (business district)
Magnificent Mile (Near North):
- Shopping and dining
- Close to Navy Pier
- Hotels: 150 to 400 dollars per night
- Busy and central
River North:
- Restaurant and gallery district
- Easy walk to Loop attractions
- Hotels: 140 to 350 dollars per night
- Good balance of local and tourist
Good Value Neighborhoods
Lincoln Park:
- Residential area with local feel
- Red Line train access
- Hotels: 100 to 250 dollars per night
- Safe, family friendly
- Historic district
- Near Museum Campus
- Hotels: 90 to 200 dollars per night
- Quieter than downtown
Areas to Avoid for Tourists
What should I know before visiting Chicago? Crime concentrates in specific areas far from tourist zones.
Avoid these neighborhoods for accommodations:
- Englewood (South Side)
- Austin (West Side)
- South Shore (South Side)
- West Garfield Park (West Side)
These areas sit miles from tourist attractions. You won’t accidentally end up there. Budget hotels in these areas offer low rates but require long commutes and present safety concerns.
Hotel Booking Tips
Book directly with hotels for best rates and flexibility. Third-party sites often charge cancellation fees.
Look for hotels near L train stops. This expands your options and saves money versus staying downtown only.
Avoid hotels more than 3 blocks from Michigan Avenue or State Street in the Loop. These fringe areas feel isolated at night.
Check hotel parking fees before booking. Downtown hotels charge 40 to 70 dollars per night for parking.
9. Navy Pier and Lakefront Activities
Navy Pier extends 3,300 feet into Lake Michigan. It attracts 9 million visitors yearly.
What to Do at Navy Pier
Centennial Wheel: 200-foot Ferris wheel, climate-controlled gondolas Cost: 18 dollars for adults Best time: sunset for views of skyline
Chicago Children’s Museum: hands-on exhibits for kids under 12 Cost: 19 dollars per person Duration: 2 to 3 hours
Cruises and boat tours: architectural tours, dinner cruises, speedboat rides Cost: 30 to 100 dollars depending on tour
Restaurants and shops: chain restaurants mostly, touristy shopping
Is Navy Pier Worth Visiting?
For families with young children: yes, the children’s museum and Ferris wheel provide entertainment.
For couples or solo travelers: skip it unless you want a specific cruise or boat tour.
The pier itself offers standard tourist shops and chain restaurants. The real value comes from the boats and views, not the pier attractions.
Better Lakefront Activities
Beaches: Chicago has 26 public beaches. North Avenue Beach and Oak Street Beach are closest to downtown.
Lakefront Trail: 18-mile path for biking, running, walking. Connects parks and beaches.
Montrose Harbor: bird sanctuary, less crowded beach, dog beach area.
Promontory Point: 31st Street, locals’ favorite for skyline views.
These free alternatives provide better Chicago experiences than the crowded, commercial Navy Pier.
10. Practical Tips: What Should I Know Before Visiting Chicago
These details help you avoid common tourist mistakes and challenges.
Weather Preparation
Chicago weather changes quickly. Lake Michigan creates sudden temperature drops and wind.
Pack layers always. A 70-degree morning can become a 50-degree afternoon near the lake.
The “Windy City” nickname refers to politics, not weather. But winds off the lake genuinely affect comfort. Bring a windbreaker even in summer.
Tipping Culture
Restaurant servers: 18% to 20% Bartenders: 1 to 2 dollars per drink Taxi and rideshare: 15% to 20% Hotel housekeeping: 2 to 5 dollars per night Valet parking: 2 to 5 dollars
Safety Awareness
Chicago tourist areas are safe. Use normal city awareness:
Don’t display expensive jewelry or electronics unnecessarily Stay in well-lit, populated areas at night Keep bags closed and phones secured Use rideshare instead of walking alone late at night
Most crime occurs in neighborhoods you won’t visit as a tourist.
Money and Costs
Chicago costs less than New York or San Francisco but more than most Midwest cities.
Daily budget ranges:
- Budget: 100 to 150 dollars (hostel, cheap eats, free attractions)
- Mid-range: 200 to 300 dollars (good hotel, nice meals, paid attractions)
- Luxury: 400+ dollars (upscale hotel, fine dining, private tours)
Phone and Internet
Free Wi-Fi available at most hotels, coffee shops, and many public spaces.
Cell service works well throughout the city on all major carriers.
Drinking and Smoking
Legal drinking age: 21, ID required Alcohol sales: until 2 AM (bars close at 2 AM or 4 AM depending on license) Public drinking: illegal on streets and beaches Smoking: banned in restaurants, bars, and public buildings
Sales Tax
Illinois sales tax: 10.25% in Chicago Restaurant tax: additional 0.5% Hotel tax: additional 17.4%
Factor these into your budget. The menu price isn’t the final price.
Vacationing in Chicago rewards those who plan ahead. The city offers world-class attractions, food, and culture. Visit in late spring or early fall for the best experience. Focus your time on museums, architecture, and neighborhoods rather than tourist traps. Use public transportation. Stay in well-located hotels. Try the food specialties. With these tips, you’ll experience Chicago like someone who knows what they’re doing.