A guide to Chicago's best architecture, lakefront parks, world-class museums, deep dish pizza, and vibrant neighborhoods across the Windy City.
Last updated:
0 of 29 completed0%
Copied!
Iconic Landmarks & Parks
Visit Millennium Park and Cloud Gate
Cloud Gate (the Bean) is a 110-ton polished steel sculpture best photographed before 9 AM when crowds are thin. The park is open daily 6 AM to 11 PM, free admission. In summer, the Jay Pritzker Pavilion hosts free concerts most evenings.
Take a photo at Cloud Gate from underneath
Walk through Lurie Garden on the south end
Step onto the Skydeck Ledge at Willis Tower
The glass-floored ledges extend 4.3 feet from the 103rd floor, 1,353 feet above the street. On clear days visibility reaches 50 miles across four states. Tickets are $28-35 for adults; booking a timed entry online saves 20-40 minutes of waiting.
Walk along Navy Pier
The pier stretches 3,300 feet into Lake Michigan. The 196-foot Centennial Wheel costs $18 per ride and runs year-round. Free fireworks shows happen Wednesday and Saturday nights from Memorial Day through Labor Day at 9:30 PM.
Ride the Centennial Wheel for skyline views
Catch a fireworks show in summer
See Buckingham Fountain in Grant Park
The fountain holds 1.5 million gallons and shoots water 150 feet in the air. It runs from mid-April through mid-October, with a 20-minute light and music show every hour from dusk to 11 PM. Grant Park itself is free and spans 313 acres.
Museums & Culture
Spend a half day at the Art Institute of Chicago
One of the largest art museums in the world with 300,000+ works across 1 million square feet. Adult admission is $32. The Impressionist gallery (rooms 240-243) and the Thorne Miniature Rooms are standout sections. Thursday evenings until 8 PM are less crowded.
See 'A Sunday on La Grande Jatte' by Seurat
Visit the Modern Wing designed by Renzo Piano
Explore the Field Museum of Natural History
Home to Sue, the largest and most complete T. rex skeleton ever found (40.5 feet long). Basic admission is $30 for adults. The museum sits in the Museum Campus along with the Shedd Aquarium and Adler Planetarium — all three are walkable within 15 minutes.
Visit the Museum of Science and Industry
The largest science museum in the Western Hemisphere, housed in the only remaining building from the 1893 World's Fair. A captured German U-505 submarine is on display — the tour inside costs $8 extra. General admission is $24.95.
Tour the Chicago History Museum
Covers Chicago from the 1871 Great Fire to the present. The Sensing Chicago gallery lets you touch artifacts and hear historical audio. Admission is $19 for adults. Located at the south end of Lincoln Park, a 5-minute walk from the zoo.
Architecture & River
Take an architecture river cruise
The 90-minute boat tours cover 50+ buildings along the Chicago River's three branches. Tickets cost $40-55 per person depending on the operator. Morning departures have softer light for photography. The tours run from late March through November.
Walk the Chicago Riverwalk
The 1.25-mile path runs along the south bank of the main branch from Lake Shore Dr to Lake St. Six connected sections (called "rooms") have different themes — the Jetty section has kayak rentals for $20-25/hour. Wine bars and restaurants line the eastern blocks.
Visit the Rookery Building lobby
Frank Lloyd Wright redesigned this 1888 building's lobby in 1905 — the ornate ironwork and glass ceiling are free to view during business hours (weekdays 8:30 AM-5 PM). Located at 209 S LaSalle St in the Loop. No ticket needed, just walk in.
Admire the Tribune Tower and its facade stones
The neo-Gothic tower at 435 N Michigan Ave has 149 stones and fragments embedded in its base from landmarks worldwide, including the Great Wall of China, the Parthenon, and the Pyramids of Giza. Walk the exterior at street level to read the plaques — free and accessible anytime.
Food & Drink
Eat deep dish pizza
Deep dish takes 30-45 minutes to bake — order immediately when you sit down. A large pie feeds 3-4 people and costs $25-35. The crust is buttery and 2-3 inches deep with cheese layered under the chunky tomato sauce.
Try a Chicago-style hot dog
The traditional build is an all-beef frank on a poppy seed bun topped with yellow mustard, neon green relish, onion, tomato, pickle spear, sport peppers, and celery salt — never ketchup. Street carts and stands charge $3-5. Portillo's locations are the most popular chain option.
Get an Italian beef sandwich
Thinly sliced seasoned roast beef piled on a long Italian roll, dipped in the cooking jus. Order it "wet" for extra juice or "dry" if you want to keep your shirt clean. Sandwiches run $8-12 at most shops. The combination with Italian sausage is the local move.
Visit a speakeasy-style cocktail bar
Chicago's cocktail scene has over 30 bars consistently ranked nationally. Many speakeasy-style spots require reservations and have unmarked entrances — look for reviews listing the exact door location. Cocktails average $16-20 in the West Loop and River North areas.
Neighborhoods Worth Wandering
Shop and eat in Wicker Park and Bucktown
The intersection of Milwaukee, North, and Damen avenues is the hub — independent boutiques, record stores, and restaurants radiate outward for about 8 blocks. The Blue Line Damen stop drops you right in the middle. Weekend brunch spots fill by 10:30 AM.
Explore Logan Square's food and bar scene
Logan Blvd between Kedzie and Sacramento has a row of 1890s greystone mansions — the longest stretch in Chicago. Milwaukee Ave heading southeast from the square has the highest concentration of bars and restaurants, with new spots opening regularly. Blue Line Logan Square stop is the anchor.
Walk the Magnificent Mile on Michigan Ave
The 13-block stretch from the Chicago River to Oak St has over 460 stores. The historic Water Tower (1869) at Chicago Ave survived the Great Fire and is free to enter. The best window displays go up in mid-November for the holiday season.
Visit Pilsen for murals and Mexican culture
The 16th St corridor has over 50 outdoor murals, many by local Mexican-American artists. The National Museum of Mexican Art on 19th St is free and has 10,000+ works. Taqueria prices in Pilsen average $2-4 per taco — some of the best and cheapest in the city.
Lakefront & Outdoors
Bike or walk the Lakefront Trail
The paved path runs 18.5 miles along Lake Michigan from Ardmore Ave to 71st St. Bike rentals from Divvy (the city bikeshare) cost $3.30 for a single 30-minute ride or $16.50 for a day pass with unlimited rides. The stretch between North Ave and Oak St beaches has the best skyline views.
Relax at North Avenue Beach
The beach house is shaped like an ocean liner and has seasonal food vendors and volleyball courts (18 sand courts, free to use). The beach is free and open from Memorial Day through Labor Day, 11 AM to 7 PM with lifeguards on duty.
Visit Lincoln Park Zoo
One of the last free zoos in the country — open 365 days a year. The 35-acre park has 200+ species. The Regenstein African Journey building and the new polar bear habitat are highlights. Parking nearby costs $20-35 in zoo lots; the Brown Line Armitage stop is a 12-minute walk.
Frequently Asked Questions
How many days do you need in Chicago?
Three to four full days covers the highlights including iconic landmarks & parks, museums & culture, architecture & river at a relaxed pace. Five or more days lets you dig into local neighborhoods and take day trips. Most first-time visitors find four days strikes the right balance between seeing enough and not feeling exhausted.
What is the best time of year to visit Chicago?
Spring and early autumn typically offer the best weather with manageable crowds. Summer brings peak tourism pricing and longer queues at popular spots. Shoulder season travel saves 20-30% on accommodation and gives you shorter lines at top attractions.
How much should I budget per day in Chicago?
A mid-range daily budget of $100-180 per person covers a comfortable hotel, two restaurant meals, and attraction tickets. Street food and local markets cut food costs significantly. Pre-booking tickets for popular sites online often saves 10-15% and lets you skip long queues.
What is the best way to get around Chicago?
Public transit handles most tourist routes efficiently and cheaply. Walking between central attractions is often faster than waiting for buses or trains during peak hours. Multi-day transit passes pay for themselves after 3-4 rides per day and remove the hassle of buying individual tickets.
Do I need to book attractions in advance in Chicago?
Top-tier attractions and museums frequently sell out during peak season so book 2-4 weeks ahead for guaranteed entry. Lesser-known sites and neighborhoods rarely require advance tickets. Morning time slots (before 10:00) are the most popular; afternoon slots after 14:00 often have shorter waits.