Chicago Travel Guide

Plan your trip to Chicago with our comprehensive travel guide featuring top attractions, activities, food, where to stay, and more.


Day 1 Visit the Art Institute of Chicago in the morning. In the afternoon, explore the Magnificent Mile and do some shopping.
Day 2 Spend the day at Navy Pier. Check out the Ferris wheel, shops, and restaurants.
Day 3 Take a walking tour of Chicago’s iconic architecture.
Day 4 Spend the day at Millennium Park and attend a concert or event in the evening.
Day 5 Explore Chicago’s museums, such as the Field Museum or the Museum of Science and Industry.
Day 6 Enjoy a Chicago-style hot dog and catch a Cubs game.
Day 7 Finish off your trip with a comedy show at The Second City improv theater.

Food and Drink Scene of Chicago

Chicago is known for its incredible food scene. These are some of the must-try dishes and local beverages:

Must-Try Dishes

  • Chicago-style hot dogs
  • Deep-dish pizza
  • Italian beef sandwiches
  • Garrett Popcorn
  • Rainbow Cone ice cream

Local Beverages

  • Malort
  • Local craft beer from Goose Island, Revolution Brewing, or Half Acre
  • The Chicago Cocktail, a variation of the Manhattan made with local bitters

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

If you’re wondering where to stay in Chicago, here are some great options:

  • The Langham, Chicago
  • The Peninsula Chicago
  • Freehand Chicago
  • HI Chicago Hostel
  • The Hoxton, Chicago
  • The Robey

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

Don’t leave Chicago without bringing home some local souvenirs and products. Some ideas include:

  • Cubs or White Sox memorabilia
  • Garrett Popcorn
  • Lou Malnati’s pizza
  • Frango Mints
  • Chicago-style beef jerky

Local Culture and Customs of Chicago

Chicagoans are friendly and welcoming people. When visiting, it’s a good idea to remember the following cultural customs:

  • Tipping is generally expected
  • Chicagoans are proud of their city and enjoy showing it off to visitors
  • The weather can be unpredictable, so be prepared for anything

Best Time to Visit Chicago

The best time to visit Chicago is during the summer months, when the weather is warm and there are plenty of events and festivals happening. However, if you’re looking to avoid crowds, consider visiting in the spring or fall.

Do’s and Don’ts of Chicago

When visiting Chicago, keep these do’s and don’ts in mind:

Do:

  • Try the deep-dish pizza
  • Take a boat tour of the architecture on the river
  • Attend a jazz or blues concert

Don’t:

  • Wear a Green Bay Packers jersey (unless you want some playful ribbing from locals)
  • Litter
  • Call it “Chi-town”

Safety and Health

Chicago is a generally safe city, but like any urban area, there are precautions to take. Here are some safety and health tips for your visit:

Safety in Chicago

  • Avoid walking alone in deserted areas
  • Keep your belongings in sight or locked up
  • Use common sense when interacting with strangers

Health in Chicago

  • Be aware of the air quality, especially during summer months
  • Stay hydrated
  • Protect yourself from mosquitoes during the summer months

Getting to Chicago: Transportation Options and Logistics

Getting to Chicago is easy thanks to a variety of transportation options:

  • Chicago O’Hare International Airport
  • Midway International Airport
  • Amtrak
  • Greyhound

How to Get Around in Chicago

Once you’re in Chicago, there are several ways to get around the city:

  • The “L” train
  • Taxis and ride-sharing services
  • Biking
  • Walking

Where to Go Next from Chicago: Nearby Destinations and Excursions

If you’re looking to explore some nearby destinations from Chicago, consider these options:

  • Milwaukee, Wisconsin
  • Indiana Dunes State Park
  • Mackinac Island, Michigan
  • Traverse City, Michigan

Conclusion

Whether you’re a first-time visitor or a seasoned traveler, Chicago is a city that will surprise and delight you at every turn. From the incredible food to the rich cultural attractions, Chicago has everything you need for an unforgettable vacation. Use our comprehensive guide to plan your trip today!

Chicago's skyline viewed from Millennium Park Chicago's skyline viewed from Millennium Park Insider tip: Winter + Snow + Wind = Chicago Insider tip: Winter + Snow + Wind = Chicago Hold on to your baby carriages in Union Station! Hold on to your baby carriages in Union Station! Three-level streets in the Loop Three-level streets in the Loop CTA trains route map CTA trains route map The Chicago The Chicago "L" rapid transit system connects the entire city A CTA bus stop: note the symbols for wheelchair accessibility and late-night hours A CTA bus stop: note the symbols for wheelchair accessibility and late-night hours Metra train on the way to the Loop Metra train on the way to the Loop Metra system map Metra system map Penguin triumphant, Lincoln Park Zoo Penguin triumphant, Lincoln Park Zoo Prairie School Style Home, Oak Park Prairie School Style Home, Oak Park Chicago River from North Michigan Avenue Chicago River from North Michigan Avenue Wentworth Ave, Chinatown's main street Wentworth Ave, Chinatown's main street The Osaka Garden on Jackson Park's Wooded Isle The Osaka Garden on Jackson Park's Wooded Isle The Lollapalooza Music Festival The Lollapalooza Music Festival Wrigley Field Wrigley Field The Gateway Theatre in Chicago/Far Northwest Side. Jefferson Park, seat of the Copernicus Foundation. The theater's Baroque spire is a replica of the Royal Castle in Warsaw. The Gateway Theatre in Chicago/Far Northwest Side. Jefferson Park, seat of the Copernicus Foundation. The theater's Baroque spire is a replica of the Royal Castle in Warsaw. The L rumbling overhead in Chicago/Loop The L rumbling overhead in Chicago/Loop Chicago's deep dish pizza is incredible Chicago's deep dish pizza is incredible Personal pan deep dish pizza. Personal pan deep dish pizza. A charred Chicago-style hot dog with all the trappings A charred Chicago-style hot dog with all the trappings A Chicago-style hot dog with duck-fat fries. A Chicago-style hot dog with duck-fat fries. The legendary Chicago Theater The legendary Chicago Theater The Trump International Hotel and Tower. The Trump International Hotel and Tower. Violent crime rates by neighborhood Violent crime rates by neighborhood The spectacular Bahá'í Temple The spectacular Bahá'í Temple


    Bridgeport-Chinatown
    Bronzeville
    Chatham-South Shore
    Far Southeast Side
    Far Southwest Side
    Far West Side
    Hyde Park
    Lakeview-North Center
    Logan-Bucktown
    Loop
    Near North
    Near West Side
    North Lincoln
    Pilsen
    Rogers Park
    Wicker Park