5-day Trip Plan Around Chicago in Autumn

Vincent Yuan · updated on Aug 26, 2023 · 6 min read

Life

I have been living in Chicagoland since I arrived in the United States, this is definitely one of the most beautiful cities in the U.S. with a lot of fun such as great museums & shows, city skylines and food etc. Also it is not far away from those attractions near Lake Michigan in other states, so it is a great place to plan for a trip of a few days.

This is a good chance for me to introduce this place that I live in and also have fun in the places around this spot. Please note that this post also includes the trip plan to other cities around Chicago for a 5-day plan, as in fact for traveling just in Chicago city, 1 to 2 days would be well enough for tourists in most cases. So please feel free to jump to the Chicago city tour if you do not have plan to go to other places.

Day 0: Pick up & Go around

Firstly, start with O'Hare Airport as this kicks off the trip and the O'Hare Airport is not boring at all. O’Hare does a good job of displaying unique public art throughout the airport. Find sculptures, murals, paintings, and more. The most popular spot is the oft-Instagrammed neon tunnel, titled The Sky’s the Limit, connecting Concourses B and C.

Also, near the O'Hare Airport, there is a huge shopping center - The Fashion Outlets of Chicago.

O'Hare Airport to The Fashion Outlets of Chicago

It is the only two-level indoor luxury outlet shopping experience in the region, featuring over 130 top designer brands such as Gucci, Prada, Versace, Burberry, and Saint Laurent.

For the rest of day, it is suggested to sort things out and take a good rest, as it will refresh yourself and help get ready for the following trips.

Day 1: Lake Geneva (1.5 hours drive)

This plan starts on weekend, so the Chicago city tour is put in the end just to avoid traffic jam and crowds in the city.

Start: Chicago, IL

End: Lake Geneva, WI

Lake Geneva, Wisconsin is the first stop of the autumn road trip, where you can enjoy the beauty of maples all around the stunning lake, walking along the lakeshore trail, cycling through the maples and exploring boutique shops, it is worth a whole day to indulge in the beautiful nature.

Day 2: Galena, IL

At the boarder of Illinois and Iowa, there is a European style town - Galena, there are tons of architectures built in 19th century. And in autumn, the mountain behind the town is also going to be covered by amazing yellow forest.

Start: Chicago, IL

End: Galena, IL

You can start by visiting the Ulysses S. Grant House which is an Italianate-style brick house with original furnishings that looks very much as it did in 1865 when a group of townspeople presented it as a gift to Ulysses S. Grant. You can also visit the Galena Country Welcome Center which provides information about the town and its attractions.

If you're looking for outdoor activities, you can go on thigh-burning hikes at Mississippi Palisades State Park. For an aerial adventure, you can try out the six ziplines and a 140-foot sky bridge at Long Hollow Canopy Tours.

For lunch, you can try out the friendly staff at Durty Gurt's Burger Joynt who sling some serious patties. The Ultimate B.C.B. comes topped with four slices of melted cheddar and six slices of bacon.

For dinner, you can try out the split-nationality menu at Fritz and Frites which consists of French and German favorites: Fritz fans load upon schnitzel, sauerbraten and spaetzle.

Day 3: Quad Cities, IL

The Quad Cities is a region of cities in the U.S. states of Iowa and Illinois: Davenport and Bettendorf in southeastern Iowa, and Rock Island, Moline and East Moline in northwestern Illinois.

Start: Galena, IL

End: Quad Cities, IL

This is one of the best points to witness the spectacular view of Mississippi River. One good option it to take the Celebration River Cruises in Moline.

Home

Celebration Belle

Day 4 - 5: Chicago Metropolitan Area, IL

So finally back home! Chicago city and suburbs also worth one to two days of visiting. Mostly, the museums and city sightseeing would be the way to experience Chicago.

Chicago is a great city to visit in autumn. There are many things to do and see in Chicago in two days. Here is a suggested itinerary for you:

First day:

Visit the Art Institute of Chicago which features nearly 300,000 works from all over the world in its permanent collection. You’ll find pieces created in the Byzantine era, as well as paintings completed just a few decades ago. Highlights include Jacob Lawrence’s The Wedding, Georgia O’Keeffe’s Sky above Clouds IV and Grant Wood’s American Gothic. In fact, besides Art Institute of Chicago, there are a few famous museums or aquariums, kindly check out the links in the appendix.
Millennium Park and Cloud Gate are also worth visiting. The park is home to several art installations and sculptures, including the famous Cloud Gate sculpture (also known as The Bean).

Second day:

Take a stroll along the Chicago Riverwalk. The Riverwalk is a pedestrian path along the Chicago River that offers great views of the city skyline. There are also several restaurants and bars along the way where you can stop for a drink or a bite to eat.
Navy Pier is another popular attraction in Chicago. It’s a great place to take a walk and enjoy views of Lake Michigan.

There are also famous opera or festivals in Chicago shared in the appendix.

Conclusion

In summary, in Chicago and the places around, there are both nature attractions and cultural places to experience, I really enjoy the life here. Hopefully this post helps you for the trip to Chicago!

Appendix

Here are some famous museums and aquarium in Chicago and their ticket links:

The Art Institute of Chicago: https://www.artic.edu/visit-us
The Field Museum: https://www.fieldmuseum.org/visit
The Museum of Science and Industry: https://www.msichicago.org/visit/tickets/
The Museum of Contemporary Art: https://mcachicago.org/Visit/Tickets
Shedd Aquarium: https://www.sheddaquarium.org/plan-a-visit/get-tickets

Here are some of the famous musical festivals and opera in Chicago along with their official websites on the Chicago government website.

Chicago Air and Water Show
Chicago Blues Festival
Chicago Gospel Music Festival
Chicago House Music Festival and Conference
Chicago Jazz Festival
Chicago SummerDance
Lollapalooza
Heatwave
Pitchfork Music Festival
Arc Music Festival
Riot Fest