Toll Roads Chicago Map

Introduction

Chicago is a bustling city known for its architecture, museums, and deep-dish pizza. But did you know that it’s also home to a network of toll roads that can take you to some of the most exciting destinations in and around the city? In this travel guide, we’ll explore the best toll roads in Chicago and the attractions and activities they lead to. Whether you’re a local or a visitor, you’ll discover something new and exciting on these scenic routes.

Top Attractions

The Magnificent Mile

One of the most iconic toll roads in Chicago is the Magnificent Mile, a stretch of Michigan Avenue lined with luxury boutiques, department stores, and restaurants. Take a drive down this road to see some of the city’s most impressive architecture and enjoy the bustling energy of the street.

Chicago Botanic Garden

For a peaceful escape from the city, head north on the Tri-State Tollway to the Chicago Botanic Garden. This 385-acre garden is home to over 2.6 million plants and offers a variety of walking trails, gardens, and events throughout the year.

Indiana Dunes National Park

If you’re willing to venture a bit further from the city, take the Skyway toll road to Indiana Dunes National Park. This beautiful park offers over 15 miles of beaches, hiking trails, and stunning views of Lake Michigan.

Hidden Gems

Illinois Route 53

For a scenic drive through the suburbs, hop on Illinois Route 53. This toll road takes you through charming neighborhoods and offers glimpses of hidden parks and forest preserves.

Elgin-O’Hare Expressway

The Elgin-O’Hare Expressway may be one of the city’s lesser-known toll roads, but it offers access to some hidden gems. Take this road to explore the Schaumburg area, where you’ll find the Legoland Discovery Center and Medieval Times dinner theater.

Food Scene

Chicago-style Hot Dogs

No trip to Chicago is complete without trying a Chicago-style hot dog. Take the Kennedy Expressway to Portillo’s, a local institution known for their delicious hot dogs, Italian beef sandwiches, and chocolate cake.

Deep-dish Pizza

Another Chicago classic is deep-dish pizza. Take the Tri-State Tollway to Lou Malnati’s, one of the city’s most famous pizza joints. Their buttery, flaky crust and gooey cheese will satisfy any pizza lover’s cravings.

Budget-Friendly Tips

Weekday Discounts

If you’re looking to save some money on tolls, try traveling on weekdays instead of weekends. Many toll roads offer discounts for weekday travel, so plan your trip accordingly.

I-PASS

Investing in an I-PASS transponder can also save you money on tolls. This electronic device allows you to travel through toll booths without stopping and often offers lower toll rates than cash payments.

Outdoor Adventures

Starved Rock State Park

Take the I-355 toll road south to Starved Rock State Park, where you’ll find 13 miles of hiking trails, waterfalls, and stunning views of the Illinois River.

Morton Arboretum

If you’re looking for a more relaxed outdoor experience, head west on the Reagan Memorial Tollway to the Morton Arboretum. This 1,700-acre arboretum offers walking trails, gardens, and a variety of events throughout the year.

Family-Friendly Activities

Brookfield Zoo

Take the Tri-State Tollway south to Brookfield Zoo, where you’ll find over 216 acres of exhibits and attractions for animal lovers of all ages.

Exploritorium

For indoor fun, head to the Exploritorium in Skokie. This hands-on children’s museum offers a variety of exhibits and activities that encourage learning and creativity.

Off-the-Beaten-Path Experiences

Pleasant Prairie Premium Outlets

Take the Tri-State Tollway north to Pleasant Prairie, Wisconsin, where you’ll find the Pleasant Prairie Premium Outlets. This outdoor shopping center offers over 90 stores and is a great destination for bargain hunters.

Chain O’Lakes State Park

For a unique outdoor experience, take the I-94 toll road north to Chain O’Lakes State Park. This park offers over 6,000 acres of waterways and is a popular destination for boating, fishing, and camping.

Natural Wonders

Illinois Beach State Park

Take the Tri-State Tollway north to Illinois Beach State Park, where you’ll find over 4,160 acres of sand dunes, wetlands, and prairies. This park is home to a variety of wildlife and offers stunning views of Lake Michigan.

Morton Arboretum

The Morton Arboretum is not only a great destination for outdoor enthusiasts but also a hotspot for natural wonders. Take a walk through the arboretum’s gardens and forests to see a variety of unique trees, plants, and wildlife.

Vibrant Nightlife

Rosemont Entertainment District

Take the Tri-State Tollway to the Rosemont Entertainment District, where you’ll find a variety of bars, restaurants, and entertainment venues. Catch a show at the Allstate Arena or enjoy a cocktail at the Fashion Outlets of Chicago.

Wrigleyville

For a more laid-back nightlife experience, head to Wrigleyville, the neighborhood surrounding Wrigley Field. This area offers a variety of bars and restaurants and is a great destination for sports fans.

Local Markets

Chicago French Market

Take the Kennedy Expressway to the Chicago French Market, where you’ll find a variety of vendors selling fresh produce, baked goods, and artisanal foods.

Maxwell Street Market

For a more traditional market experience, head to the Maxwell Street Market. This outdoor market offers a variety of vendors selling clothing, jewelry, and street food.

Beaches and Mountains

Indiana Dunes National Park

As mentioned earlier, Indiana Dunes National Park offers over 15 miles of beaches and stunning views of Lake Michigan. Spend a day lounging on the sand or hiking through the dunes.

Mount Baldy

For a unique mountain experience, head to Mount Baldy, a 126-foot sand dune located in Indiana Dunes National Park. Hike to the top for stunning views of the lake and surrounding landscape.

Cultural Immersion

Chinatown

Take the Dan Ryan Expressway to Chinatown, where you’ll find a variety of restaurants, shops, and cultural attractions. Visit the Chinatown Gate and the Chinese-American Museum of Chicago to learn more about the neighborhood’s history and culture.

Pilsen

For a taste of Chicago’s vibrant Latino culture, head to Pilsen. This neighborhood offers a variety of murals, galleries, and restaurants that showcase the area’s rich history and traditions.

Art and Music Scene

Art Institute of Chicago

Take the Kennedy Expressway to the Art Institute of Chicago, one of the city’s most famous museums. This museum houses a variety of art collections and exhibitions and is a must-visit for art lovers.

Chicago Symphony Orchestra

For a night of music, head to the Chicago Symphony Orchestra. This world-renowned orchestra performs a variety of classical and contemporary pieces throughout the year.

Walking Tours

Chicago Riverwalk

Take a stroll along the Chicago Riverwalk, a pedestrian path that runs along the Chicago River. This walk offers stunning views of the city’s architecture and a variety of restaurants and bars.

Chicago Pedway

For a unique walking experience, explore the Chicago Pedway, a series of underground tunnels and walkways that connect various buildings and landmarks in the city.

Architectural Marvels

Willis Tower

Take the Kennedy Expressway to the Willis Tower, one of Chicago’s most famous skyscrapers. This building offers stunning views of the city and is home to a variety of offices and restaurants.

Frank Lloyd Wright Home and Studio

For a taste of Chicago’s architectural history, head to the Frank Lloyd Wright Home and Studio in Oak Park. This house and studio offer guided tours and a glimpse into the life and work of one of America’s most famous architects.