Top Attractions for First-Timers

With so many things to see and do in Chicago, narrowing down your options can be tricky for a first-time visitor. To help you out, we’ve highlighted some of the top sites and activities in six popular categories. Use this list to get inspiration when putting together your Chicago itinerary.


Chicago is renowned for its diverse and distinctive architecture. Some must-see buildings and areas include: – Willis Tower Skydeck – Take in panoramic views of the city from 1,353 feet up at Chicago’s tallest building. This observatory also has fun attractions like The Ledge, a series of glass boxes jutting out of the building where you can step out and look straight down. – Wrigley Building – Check out this iconic 1920s skyscraper modeled after Seville’s Giralda Tower. Its white terra cotta exterior makes it stand out on the Chicago River. – Frank Lloyd Wright Home and Studio – Tour the workplace of influential architect Frank Lloyd Wright and see examples of his Prairie Style architecture. – Chicago Cultural Center – This National Historic Landmark showcases elaborate stained glass domes and mosaics. Free tours are available.


Immerse yourself in art, history, and culture by exploring some of Chicago’s world-class museums like: – The Art Institute of Chicago – See an incredible collection of Impressionist and Post-Impressionist paintings, plus American classics like American Gothic. Field Museum of Natural History – Explore Egyptian mummies and massive dinosaur skeletons at this lakefront museum. Museum of Science and Industry – Get hands-on with exhibits on everything from genetics to aeronautics. Especially great for kids. National Museum of Mexican Art – Discover contemporary and traditional Mexican art and culture in Pilsen. Museum of Contemporary Art – View modern painting, sculpture, photography and film in a Ludwig Mies van der Rohe building.


Don’t let Chicago’s big city status fool you – it also boasts fantastic green spaces. Top parks and gardens include: – Millennium Park – Chicago’s crown jewel of public spaces. Snap a pic by “The Bean” sculpture and stop to smell the blooms in the Lurie Garden. Grant Park – Sprawling green space with Buckingham Fountain as its centerpiece. Also home to the Art Institute and Museum Campus. Maggie Daley Park – This downtown park has rock climbing walls, rollerblading, and creative playscapes perfect for kids. Lincoln Park – Chicagoans flock to this huge public park featuring a zoo, conservatory, lakeshore trails, and Chicago History Museum. Garfield Park Conservatory – Escape winter in Fern Room’s lush tropical plants and relax among spring flowers in the Palm House.


A trip to Chicago isn’t complete without diving into some quintessential Midwest cuisine. Be sure to try: – Deep dish pizza – Stop by Lou Malnati’s, Pequod’s, or Giordano’s for authentic deep dish. – Chicago-style hot dogs – These famous hot dogs come loaded with mustard, relish, onions, tomatoes, peppers, and a pickle spear. – Italian beef sandwiches – Thinly sliced roast beef is served juicy on a French roll at iconic spots like Portillo’s. – Garrett Popcorn – See why Chicagoans line up for the city’s famous caramel and cheese popcorn mix. – Harold’s Chicken Shack – This fried chicken chain is a taste of the real Chicago. The mild sauce is a must.


When the sun goes down in the Windy City, the nightclubs and comedy venues come to life. Favorite spots include: – Second City – This legendary comedy club launched careers of Tina Fey, Stephen Colbert, and more. – Kingston Mines – Swing by this Lincoln Park blues club for live music 365 days a year. – Green Mill – Historic Art Deco hotspot where Al Capone used to frequent and famous jazz musicians still play. Underground Wonder Bar – Enjoy craft cocktails and dancing in River North at this lively speakeasy-themed bar. Late Bar – One of the best bars for night owls, staying open until 4AM Friday and Saturday in Lakeview.

Lakefront Activities

Make time during your visit to enjoy Chicago’s beloved Lake Michigan waterfront. Top spots include: – Navy Pier – Ride the Ferris Wheel or catch a show at this lively pier filled with attractions and restaurants. North Avenue Beach – Chicago’s most popular beach with volleyball, kayaking, and stunning lakefront views. Lakefront Trail – Walk, run or bike this 18-mile path with beautiful views of the skyline and lake. Kayaking – Paddle under the Chicago River’s famous movable bridges and along the city’s canals. Architecture Boat Tour – See Chicago’s iconic architecture from the water on an informative river cruise.

Family Fun

Chicago offers tons of great activities for families traveling with kids. Add these to your itinerary: – Shedd Aquarium – Get nose-to-nose with sharks, dolphins and penguins right next to Lake Michigan. Willis Tower Skydeck – Let kids experience The Ledge’s thrilling glass boxes hanging over the city. Museum of Science & Industry – Hands-on exhibits like a real Boeing 727 will occupy kids for hours. Lincoln Park Zoo – One of the oldest zoos in the country with a children’s zoo and farm. Free admission. Maggie Daley Park – Fun recreational attractions like rock climbing walls and mini golf.

How to Get Around Chicago

Now that you know the best places to visit in Chicago, let’s discuss your transportation options for getting around the city efficiently.

Public Transportation

Chicago has an extensive public transportation system called the “L” with color-coded rail lines and affordable fares. It’s efficient for getting almost anywhere you want to go, especially downtown. Buy a Ventra fare card at stations to pay for trains and buses. The CTA website has a trip planner to map routes. Take the Red Line for many top sites like Willis Tower, the Art Institute, Wrigley Field and more. The Blue Line reaches buzzing neighborhoods like Wicker Park and Logan Square. Google Maps integrates transit too and will guide you. The L generally runs from 4am to 1am during the week, with more limited hours on weekends. Know when the last train is before your night out ends!

Taxis and Rideshares

When the L doesn’t run to your destination or you don’t want to walk far, taxis and rideshares fill the gaps. You can hail a cab downtown but will need to call a dispatcher in outer neighborhoods. Uber and Lyft both operate throughout Chicago. Fares add up quickly though, especially during rush hour or high-demand times. Pool options can save money. Compare estimated prices among rideshares and taxis before booking. Also factor in potential surge pricing with rideshares at peak times. Taxis have set rates but require cash or booking ahead through apps like Curb. Shared rides are not an option. Know both rideshare and taxi fares vary greatly depending on traffic.

Charter Buses

For hassle-free transportation around Chicago with medium or large groups, charter buses can’t be beat. No coordinating payment or meetup spots—just hop on board together! Charter buses range from midsize 25-passenger minibuses to spacious 56-passenger coaches equipped with cushy seats, climate control, bathrooms, entertainment systems, and more. Charter buses allow groups to stay together in comfort and style while seeing Chicago’s top sites. No need to rely on public transit schedules or get stuck in traffic. Your professional driver handles it all! Arrange direct transport between yourhotel, the airport, attractions, restaurants – wherever your itinerary takes you. Charter bus services like Chicago Party Bus Company offer hourly rates or full-day rentals.

Ready to Get Started?

We hope this Chicago first-timer’s guide gets you excited to explore the amazing attractions and flavors this world-class city offers. With so many things to do from museums to restaurants, stunning lakefront views to lively nightlife, the challenge is fitting it all into one visit! Use our spotlight on top sightseeing categories to build your custom Chicago itinerary. Mix and match favorites to create your perfect blend of arts, culture, food, recreation and family time. Then let Chicago Party Bus Company handle the transportation by booking comfortable, convenient charter buses for your group. Our team makes getting around Chicago simple and stress-free, so you can focus on making unforgettable memories. Ready for your fantastic first Chicago experience? Call us at 224-307-8900 or request a quote online to get the trip-planning started! From helping you choose the right buses to answering all your questions, we’re here to help every step of the way.