Aside from its famous skyline, Chicago is a city of endless layers. Whether you’re an architecture buff, a foodie hunting for the best deep dish or a family looking for fun, the list of places to visit in Chicago is massive. To truly experience the city, you need to explore both the main attractions downtown and the vibrant neighborhoods that locals call home.
AAA acts as your trusted travel partner to help you discover these spots by handling the details for you. Your membership provides access to exclusive discounts on hotels and attractions, along with the peace of mind that comes with reliable roadside assistance.
Why Chicago’s Neighborhoods Are the Real Attraction
The landmarks in downtown Chicago are impressive, but the true soul of the city lives in its neighborhoods. You’ll find the real food and culture in places like Pilsen, Oak Park or Lincoln Square. Each neighborhood tells a special story about the immigrants and communities that built it. You get a much better meal and a more honest experience when you explore these areas.
1. Pilsen
- Location: Lower West Side
- Vibe: Colorful, artistic and rooted in Mexican heritage
- AAA Tip: Use the AAA Mobile App to find member-discounted parking near 18th Street to avoid the headache of city street sweeping tickets.
- Stay at: The AAA Four Diamond-designated Hilton Chicago
Pilsen is one of the best places to visit in Chicago because it wears its heart on its walls. It’s a walkable neighborhood famous for its 16th Street murals, where most of the brick walls of the railway embankment have been turned into works of art. You can walk the stretch between Halsted and Western Avenue to see colorful depictions of Aztec history, immigration stories and local heroes.
After you’ve worked up an appetite, head over to S.K.Y. on 18th Street for some contemporary American cuisine with Asian influences in a polished, yet relaxed setting. If you want a great night out, go to Pilsen Yards. They serve delicious Latin food and often feature live music or a DJ on their patio.
2. Bronzeville
- Location: Historic South Side (The Black Metropolis)
- Vibe: Soulful, historic and celebratory
- AAA Tip: Use AAA Trip Canvas to find the best local dining spots and plan your route to the neighborhood’s historic landmarks.
- Stay at: The AAA Four Diamond-designated Marriott Marquis Chicago
Bronzeville is the historic center of Chicago’s Black community. It grew during the Great Migration and its legacy remains today. You can start your visit just north of the neighborhood at the Prairie Avenue Historic District.
See the Gilded Age mansions before heading South to explore the public art and monuments. Sports fans can visit Rate Field, home of the Chicago White Sox. Visitors can also enjoy a Chicago Tour of the South Side to learn about the jazz legends and civil rights leaders who built this community.
The current food scene here is just as exciting as the history. Bronzeville Winery is the cultural hub, featuring live music, a great wine list and a patio that buzzes with energy. For a refined taste of the South Side, head just south to AAA Three Diamond-designated Virtue Restaurant in Hyde Park. Chef Erick Williams serves elevated Southern classics, such as blackened catfish and tender short ribs, in a warm, welcoming space.
3. Uptown
- Location: Far North Side
- Vibe: Vintage glamour, jazz roots, global eats
- AAA Tip: Save on a rental car with Hertz discounts to easily drive up the lakefront to explore the North Side.
- Stay at: The AAA Approved Hotel Versey Days Inn by Wyndham Chicago
If you want to experience one of the most famous places to visit in Chicago for music history, you have to go to Uptown. While here, you can visit the Green Mill Cocktail Lounge, a legendary jazz club where you can still sit in Al Capone’s favorite booth. You can also spend a day enjoying the outdoors along the Chicago Lakefront Trail, which even ranks among the best places to run in Chicago.
Start your night with dinner in nearby Wrigleyville before heading to the clubs. Swift Tavern serves great steaks, oysters and tavern classics overlooking historic Wrigley Field. It puts you in the perfect position to enjoy a full night of Chicago entertainment.
4. Architectural Tours
- Location: 951 Chicago Ave.
- Vibe: Living history, design inspiration
- AAA Tip: AAA Travel Advisors can help you book these popular tours in advance so you don’t miss out on the limited slots.
- Stay at: The AAA Three Diamond-designated Hyatt Lodge Oak Brook, Chicago
Architectural tours are one of the most amazing things to do in a city as unique as Chicago. Head over to the historic village of Oak Park, as it holds the world’s largest collection of Frank Lloyd Wright designs. Take it further with a walking tour that takes you inside his home and studio. You get to step directly into the laboratory where the famous Prairie Style was born.
Once you finish admiring the design, head back toward the city for a meal in the Fulton Market district. Sepia offers a AAA Four Diamond-designation and serves gourmet American cuisine inside a historic 1890s print shop, which perfectly complements the day’s theme.
5. The Hemingway Birthplace Home
- Location: 339 N. Oak Park Ave.
- Vibe: Literary, Victorian, educational
- Stay at: Carleton Of Oak Park
Lovers of literature head over to the Hemingway Birthplace Home. You’ll feel like you stepped into a time capsule because this Queen Anne Victorian home looks exactly as it did when Ernest Hemingway was born there in 1899. Tours of the Hemingway Birthplace Home show you the strict Victorian world that shaped the young author before he became a world traveler.
After exploring the turn of the century, head to Encore! by Little Gem, located just blocks away, to enjoy European-inspired dishes that fit the day’s historic theme perfectly. If you prefer a more modern vibe, Cooper’s Hawk Winery & Restaurant has a massive wine list and handcrafted American cuisine right in downtown Oak Park.
6. Brookfield Zoo
- Location: 8400 W. 31st St., Western Suburbs
- Vibe: Wild, family-oriented, expansive
- AAA Tip: Get a Free Battery & Tire Check via AAA roadside assistance benefits before you head out to the suburbs.
- Stay at: The AAA Diamond Approved Best Western Plus Chicagoland-Countryside
You’ll find the Brookfield Zoo, a 20-minute drive from the historic Oak Park district. It ranks as one of the top places to visit in Chicago for families who want room to roam. The zoo houses hundreds of species in habitats that mimic a wild and open environment. You can feed a giraffe by hand or stand nose-to-beak with a bird in the Penguin Encounter.
What’s really unique about this zoo is how hands-on its experiences are. You can take the kids to the Hamill Family Play Zoo, where they can pretend to be zookeepers and build their own habitats. If you need a crowd-pleaser for dinner, there’s a Portillo’s just down the road in North Riverside. It’s a classic spot for Chicago-style hot dogs and cake shakes after a long day of walking.
7. Lou Malnati’s Pizzeria
- Location: 1038 Lake St., Oak Park
- Vibe: Classic, hearty, relaxed
- AAA Tip: Check for AAA Dining Rewards to see if you can earn cash back or get a discount on your meal.
- Stay at: The AAA Four Diamond-designated Le Méridien Chicago - Oakbrook Center
Deep-dish pizza is arguably the regional dish of Chicago and a matter of great pride. Locals like to enjoy this meal for celebrations and gatherings with friends. Lou Malnati’s is the place to go to experience this dish and vibe, largely due to their signature flaky, buttery crust.
If it’s your first time, order the Malnati Chicago Classic. It comes loaded with lean sausage, extra cheese and sauce made from vine-ripened tomatoes. After such a heavy meal, a short drive to Le Méridien Chicago - Oakbrook Center for a comfortable and modern place to crash.
8. Oak Park Conservatory
- Location: 615 Garfield St., Oak Park
- Vibe: Lush, historic, intimate
- AAA Tip: Visit a AAA Travel Store to pick up comfortable walking shoes or a durable day bag before your trip.
- Stay at: The AAA Four Diamond-desigated theWit Chicago, a Hilton Hotel
The Oak Park Conservatory is a quiet break from the city noise and it’s easily accessible via the Blue Line "L" train. The conservatory dates back to 1914 and holds a rich collection within its Edwardian-style walls. It feels intimate and uncrowded compared to the big-city museums.
Three distinct rooms take you through Mediterranean, tropical and desert environments. Step outside to enjoy the water features and native gardens if the weather holds up. Since the conservatory sits right near the train line and the highway, you can easily head back toward the West Loop for dinner. Stop at the AAA Three Diamond-designated Girl & the Goat if you prefer a lively atmosphere with small plates.
9. Chicago’s Must-See Icons That Are Worth the Crowd
While it’s fun to find hidden local spots, some landmarks are famous for a good reason. These icons define the city’s energy and skyline, so you just haven’t truly seen Chicago until you check at least a few of the following off your list:
- Grant Park: One of the best parks in Chicago, this expansive green space serves as the city’s front lawn and gathering place. There are also plenty of free things to do, like watching a concert at the Jay Pritzker Pavilion or simply strolling through the gardens to admire the impressive public art.
- The Bean (Cloud Gate): This is a shiny steel sculpture that’s a great photo opportunity in the city. Don’t miss walking underneath its arch to see your reflection warped against the skyline.
- The Art Institute of Chicago: This is one of the best museums in Chicago, housing one of the largest collections of Impressionist and Post-Impressionist art in the world. You can spend hours getting lost in the galleries, seeing masterpieces you have only ever seen in textbooks.
- A Chicago Architecture River Cruise: This is one of the most unique ways to learn about the city’s history. A boat tour offers a relaxing, front-row view of the skyscrapers that made Chicago famous.
- Skydeck Chicago: This is the place to go for beautiful skyline views from the Willis Tower. You can step out onto “The Ledge,” a glass box that extends four feet outside the building for a terrifyingly cool view of the street below.
Best Time to Visit Chicago
For the perfect balance of mild weather and manageable crowds, plan your trip for the shoulder seasons. The months of April through May and September through October are ideal because the temperatures are comfortable enough for walking all day, but you won’t have to fight the peak-season tourist boom. You’ll also find that hotel prices drop drastically after the holidays.
Summer is full of fun events and days at the beach, but things cost more and lines are longer at popular places. Winter in Chicago isn’t for the faint of heart, but it does have its own unique charm. The festive markets and holiday lights make the city feel magical despite the freezing temperatures. The cold weather means you can’t spend as much time outside, but you can still find plenty of indoor things to do in Chicago.
Plan A Smarter Chicago Trip with AAA
You’ll find the best places to visit in Chicago when you step off the beaten path and start exploring like a local. While this guide covers the highlights, there are still countless things to do in Chicago that you can discover simply by wandering down a new street.
A AAA membership can help make your trip even smoother. With it, you get things like Roadside Assistance for peace of mind, exclusive discounts on hotels and attraction tickets and much more. Start planning your getaway today to see how much you can save on your next adventure.