Tips for Planning a Trip to Chicago in the Fall

When you’re planning a trip to the Windy City, there are many fun and exciting places to consider seeing and visiting. You’ll be thinking about what foods you want to try, where you want to stay, and what you want to do while you’re visiting. Planning out your stay beforehand will help your vacation go smoothly and help you make the most of your trip.

The fall season is a perfect time to visit Chicago. The air is cooler, and the leaves are starting to change colors. There’s plenty of fun fall activities, with seasonal festivities and outdoor activities in abundance. 

To help you plan your fall trip to Chicago, we’ve compiled a list of tips.

Plan memorable Chicago experiences

Everybody has something they want to see and experience when they come to Chicago. Some people want to go to concerts, while others plan to visit as many art museums as they can. You’ll want to plan according to your interests, and the interests of others who are traveling with you. That way, everyone can have an enjoyable time during their trip to Chicago. Plus, it’ll help you decide which activities you should prioritize.

During the fall, there are various activities for people with different types of interests. For sports fans, the Bears, Bulls and Blackhawks are playing during the season. If you love to explore museums, you can visit the Field Museum to see the exhibits or the Art Institute of Chicago and see the galleries there. There is also a selection of Broadway shows and other theatrical performances to choose from in Chicago’s theater district.

A popular time to visit Chicago during the fall is Thanksgiving. During Thanksgiving time, there are lots of fun activities to do. Exciting options include the Thanksgiving Day Parade and the Museum of Science and Industry’s Christmas Around the World tree displays. If the weather turns sour during your November stay, you can always plan to do some of Chicago’s unique indoor activities. 

Take advantage of public transportation

While planning your trip, don’t forget about the numerous options for public transportation in Chicago. Some options for traveling around the city include a bike share program, taxis, elevated trains, ride-sharing, and even water taxis. 

Planning to use any of these public transportation options can help you see the city in a unique way—and you won’t have to worry about renting or parking a car. Since the fall weather is cooler, but not yet freezing, you can enjoy the outdoors by riding a bike around town.

Book your hotel based off of location

When booking a hotel for your trip, you’ll want to think about choosing a hotel that’s close to an area you would like to visit. For example, many people choose to book hotels near Magnificent Mile, a popular shopping destination. Magnificent Mile is also close to Navy Pier, has easy access to public transportation, and has many great dining options.

If you have a specific place you would like to stay, you’ll want to consider booking your hotel far enough in advance so that the hotel isn’t sold out, especially if your trip is during the fall season since more people choose to travel during the holidays.

Make dining reservations beforehand

Before your trip begins, you should research top restaurants in Chicago. If you book your dining before your trip, you can have a unique culinary experience.

For those visiting Chicago who want to try new foods, many restaurants offer seasonal menu items during the fall or have celebrations during the holidays. By booking your dining reservations in advance, you’ll ensure that you can try every restaurant on your Chicago bucket list, no matter how long the waitlist is at a restaurant. 

If you follow these tips, you can plan an unforgettable itinerary for your trip to Chicago this fall. When you visit Chicago, you’ll be able to have fun and memorable experiences if you plan out which activities you’d like to participate in. You can choose to use public transportation so that you can see the city in a unique way. Booking your hotel and dining reservations ahead of time can help you eliminate any last-minute stress you may have about your trip.

Need a place to stay when visiting Chicago? Book your reservation here.