Chicagoland Travel Guide

Discover Chicagoland with our comprehensive travel guide featuring must-visit places, hiking and biking routes, food and drink scene, where to stay, and transportation options.


Introduction to Chicagoland

Chicagoland, located in the Midwest region of the United States, is a vibrant and diverse metropolitan area with a rich history, stunning architecture, world-class museums, and vibrant neighborhoods. The region spans over 10,000 square miles and includes the city of Chicago, surrounding suburbs, and smaller towns along Lake Michigan. Whether you’re interested in exploring the city’s cultural and historical landmarks, hiking or biking its scenic trails, or taking part in exciting outdoor activities, Chicagoland has something to offer for every traveler.

List of Places to Visit in Chicagoland

Here’s a list of must-visit attractions in Chicagoland:

Culturally Important Attractions: Museums and Historical Places

  • Art Institute of Chicago: One of the top museums in the world, housing over 300,000 artworks from around the globe.
  • The Field Museum: Discover natural wonders and cultural artifacts from around the planet.
  • Museum of Science and Industry: Hands-on exhibits for all ages, including a full-sized WWII submarine.
  • The Shedd Aquarium: One of the largest indoor aquariums in the world, home to over 32,000 aquatic animals.
  • The Chicago History Museum: Explore Chicago’s past, from the stories and events that shaped the city.
  • The Frank Lloyd Wright Home and Studio: Step inside the world of the famous architect and explore his creations.
  • The Pullman National Monument: Site of the historic Pullman Palace Car Company, which played a significant role in American industrial history.

Natural Attractions of Chicagoland: Outdoor Adventures and Scenic Views

  • Millennium Park: Home to the iconic Cloud Gate (aka “The Bean”), as well as the Jay Pritzker Pavilion, Lurie Garden, and more.
  • The Lakefront Trail: A scenic running and biking path along the shores of Lake Michigan.
  • Navy Pier: A lively amusement park with carnival rides and attractions, shops, and restaurants.
  • Lincoln Park: A sprawling park with a zoo, conservatory, and a 35-acre nature museum.
  • Garfield Park Conservatory: One of the largest conservatories in the country, featuring thousands of plant species.
  • Starved Rock State Park: A nature lover’s paradise with countless hiking trails, waterfalls, and canyons.

Hiking/Biking Routes of Chicagoland

Chicagoland offers a variety of scenic hiking and biking trails, including:

  • The Illinois Prairie Path: A 61-mile trail through the western suburbs with plenty of stops and natural beauty.
  • The Des Plaines River Trail: A 56-mile trail with picturesque views of the Des Plaines River.
  • Kankakee River State Park: A 7000-acre park with hiking and biking trails along the Kankakee River.
  • The Lakefront Trail: A 18-mile path along Lake Michigan with stunning lake and city views.

Best Things to Do in Chicagoland: Activities and Tours

Make the most of your trip to Chicagoland with these exciting activities and tours:

  • Chicago Segway Tours: Take a Segway tour of the city and explore its top sights.
  • Chicago Architecture River Cruise: Learn about the city’s history and architecture with this scenic boat tour.
  • Chicago Food Tours: Sample the city’s best food while sightseeing with a guided food tour.
  • Skydeck Chicago: Get a bird’s eye view of the city from the top of the Willis Tower.
  • Chicago Helicopter Experience: See the city from above with a thrilling helicopter tour.
  • Chicago Beer Experience: Sip on local craft beers while exploring the city’s breweries.

Week-Long Itinerary for Chicagoland

Day 1: Explore downtown Chicago, including Millennium Park and the Art Institute.

Day 2: Discover the city’s architecture with a guided river cruise or Segway tour.

Day 3: Visit some of the city’s top museums, including the Field Museum and Museum of Science and Industry.

Day 4: Head to one of the nearby state parks for a day of hiking and outdoor adventures.

Day 5: Check out some of the city’s vibrant neighborhoods, such as Wicker Park, Lincoln Park, or Pilsen.

Day 6: Take a food tour of the city, sampling some of its famous dishes and drinks.

Day 7: Spend your last day exploring Navy Pier, one of the most popular attractions in the city.

Food and Drink Scene of Chicagoland

Chicagoland is known for its hearty and delicious food, with a focus on meats and classic dishes. Here are some must-try dishes and local drinks:

Must-Try Dishes

  • Chicago-style hot dog: A steamed hot dog with yellow mustard, relish, onions, tomatoes, and a pepperoncini on a poppy seed bun.
  • Deep dish pizza: A thick, cheesy pizza with a high crust, sauce on top of the cheese, and toppings galore.
  • Italian beef: A sandwich made with thin slices of seasoned beef, topped with sweet peppers and giardiniera (a blend of pickled vegetables).
  • Maxwell Street Polish: A grilled sausage served on a bun with grilled onions and mustard.

Local Beverages

  • Chicago-style beer: Try local brews such as Goose Island or Half Acre.
  • Old Fashioned: A classic cocktail made with whiskey, bitters, and sugar.

Where to Stay in Chicagoland: Hotels, Hostels, and Guesthouses

Chicagoland offers a wide range of accommodations, from luxurious hotels to budget-friendly hostels. Here are some of the top options:

  • The Langham, Chicago: A luxurious hotel located in a landmark skyscraper with river views.
  • Hotel Lincoln: A boutique hotel in Lincoln Park with a rooftop bar and stunning views of the city.
  • Freehand Chicago: A trendy hostel in River North with private and shared rooms.
  • The Robey: A stylish hotel in Wicker Park housed in a former office building with a rooftop lounge.

What to Buy in Chicagoland: Souvenirs and Local Products to Bring Home

When in Chicagoland, be sure to check out these local shops and products:

  • Garrett Popcorn: Known for its delicious and addictive “Chicago Mix” popcorn.
  • Intelligentsia Coffee: A local coffee roaster with cafes around the city.
  • Chicago Cubs or Chicago White Sox gear: Show your team spirit with some official merchandise.
  • Gino’s East Pizza Kit: Bring home a kit from one of the city’s famous deep dish pizza restaurants.

Local Culture and Customs of Chicagoland

Chicagoans are known for their friendly and welcoming nature, with a strong pride in their city and its history. Tipping is customary for most services, typically 20% for restaurants and 15-20%% for taxis or other services. It’s also important to be respectful of the city’s diverse population and communities.

Best Time to Visit Chicagoland

The best time to visit Chicagoland is during the summer months (June-August) when the weather is mild and there are numerous festivals and outdoor events happening around the city. Fall (September-November) is also a great time to visit, with cooler temperatures and beautiful fall foliage.

Do’s and Don’ts of Chicagoland

Do:

  • Do visit some of the city’s vibrant neighborhoods, such as Wicker Park, Lincoln Park, or Pilsen.
  • Do try some of the famous local dishes, such as deep dish pizza and Chicago-style hot dogs.
  • Do bring comfortable shoes – Chicagoland is a very walkable city.
  • Do take a river cruise or helicopter tour for a unique perspective of the city.

Don’t:

  • Don’t visit during the winter months (December-February) unless you’re prepared for cold temperatures and snow.
  • Don’t skip the city’s museums and cultural landmarks – they’re some of the best in the world.
  • Don’t forget to tip for most services.

Safety and Health

Safety in Chicagoland

As with any large city, it’s important to be aware of your surroundings while in Chicagoland. Some areas, particularly on the south and west sides of the city, can be more dangerous than others. However, most areas of the city and suburbs are safe for tourists. It’s also important to take precautions while walking alone at night and to keep valuables out of sight.

Health in Chicagoland

Chicagoland has a high-quality healthcare system, with numerous hospitals and clinics in the city and suburbs. It’s also important to stay well-hydrated during the summer months and to protect your skin from the sun.

Getting to Chicagoland: Transportation Options and Logistics

Airports Near Chicagoland

The two main airports serving Chicagoland are O’Hare International Airport and Midway International Airport. Both airports offer various transportation options to get to the city, including taxis, ride-sharing services, and public transportation.

Bus Stations Near Chicagoland

If you prefer traveling by bus, you can take Greyhound or Megabus to the Chicago Greyhound Bus Station or the Megabus stop in Chicago.

Other Options

If you prefer driving, Chicagoland is well-connected to several major highways, including I-90, I-294, and I-55. You can also take the Amtrak train to Union Station in Chicago or the Metra commuter train to various suburbs of the city.

How to Get Around in Chicagoland

Chicagoland offers a variety of transportation options, including:

  • The “L” train: An efficient way to travel around the city and suburbs.
  • Taxis and ride-sharing services: Available throughout the city and suburbs.
  • Buses: An affordable option for traveling to different parts of the city.
  • Biking: Chicagoland offers numerous bike trails and bike sharing programs.
  • Walking: Many neighborhoods in the city and suburbs are very walkable.

Where to Go Next from Chicagoland: Nearby Destinations and Excursions

If you have more time in the Midwest, here are some nearby destinations and excursions to consider:

  • Milwaukee, Wisconsin: Just a two-hour drive from Chicago, Milwaukee offers a lively downtown area, a beautiful lakefront, and numerous festivals and events.
  • Indiana Dunes National Park: Located along the shores of Lake Michigan, this national park is a perfect destination for beachgoers and nature lovers.
  • Galena, Illinois: A charming historic town located in the rolling hills of northern Illinois, Galena is known for its beautiful architecture and scenic trails.
  • Mackinac Island, Michigan: A picturesque island located in Lake Huron, Mackinac Island is famous for its fudge shops and horse-drawn carriage rides.

Conclusion

Chicagoland is a vibrant and exciting destination for travelers looking to experience the best of the Midwest. From world-class museums and cultural landmarks to scenic hiking trails and delicious food, Chicagoland has something for everyone. Whether you’re planning a week-long trip or a quick weekend getaway, this comprehensive tour guide will help you make the most of your time in this amazing region.

Aerial photograph of the skyscrapers at the Loop area of Chicago Aerial photograph of the skyscrapers at the Loop area of Chicago Metra system map Metra system map A Metra train pulls out of Union Station in Chicago A Metra train pulls out of Union Station in Chicago


    Chain O' Lakes
    Chicago
    Far North Suburbs
    Fox River Valley
    Inner Suburbs
    Kankakee Area
    North Shore
    Northwest Suburbs
    South Suburbs
    Western Suburbs