3 Days in Chicago This Fall

October 4, 2021

Don your favorite cozy fall sweaters and step out into the Windy City to see pumpkin lights at the pier, unimaginable fall colors at The Morton Arboretum, and fascinating sights on the night crime tours.

Check out the best places for scenic skylines or deep-dish pizza, it's all in our 3-day guides to Chicago, Illinois.

Serene or Spooky?

Need some time to relax in nature and step away from the computer? Or are you craving a heart-throbbing spooky weekend?

Whether you want a Leisurely Weekend Getaway, Moderately-Paced Itinerary, or an Action-Packed Adventure, we've got your three-day Chicago fall trip covered!

ground view of people walking past cloud gate bean in Millennium Park in Chicago, Illinois, USA

Leisurely Getaway Weekend

Where to Sleep: Hotel Versey

Hotel Versey is bright, trendy, casual hotel with a hip lobby full of board games. Located close to Lincoln Park.

Day One

Where to Go: Sky Deck Chicago

First things first, get a good look at the city you just arrived in. Head to Sky Deck Chicago and climb up to the 103rd floor of the former Sears Tower for clear observation boxes and views extending to four states.

Where to Eat Lunch: Beatnik on The River

Beatnik on The River is a funky, colorful riverside restaurant that offers a global menu, spacious seating options, and a beautiful ambiance.

Related Post: Chicago for Kids: The Ultimate Parent’s Guide

Where to See Pumpkins: Navy Pier

Walk across the Chicago RiverWalk for stunning views of the city until you reach the Navy Pier.

At the Navy Pier, ride the Ferris wheel or hop on the swings.  See more than a thousand pumpkins lit up at the Pier Pumpkin Lights, running every Saturday between October 9 - October 30. Costume contests, scavenger hunts, and Halloween movies are sure to get everyone in the fall spirit.

Day Two

Where to Eat Breakfast: Salonica Restaurant

Salonica Restaurant is a Greek diner that serves a classic hearty breakfast that you’ll be very thankful for as you walk around the museum, an eight-minute walk away.

Related Post: A Visitor’s Guide to Getting Around Chicago

Where to Explore: Museum of Science and Industry

Museum of Science and Industry is the Western hemisphere’s largest science museum. Hands-on, interactive exhibits that are thoroughly engaging for kids and absolutely fascinating for adults. Life-sized submarines, WWII planes, Tesla Coil, a coal mine, a flight simulator, an IMAX theater, a mirror maze, a fairy castle. This museum has it all.

Where to Take an Afternoon Stroll: The Magnificent Mile

Head north over the Chicago River to get to Chicago’s premier commercial district, The Magnificent Mile. A vibrant, bustling street known for shops, bars, restaurants, and posh hotels, this street offers many excitements for both adults and kids. Build a doll version of yourself at the American Girl Place, visit the Disney Store, or get some candy at Dylan’s Candy Bar. You can also admire views of the Chicago Water Tower, the Wrigley Building, and the John Hancock Center. 

Day Three

Where to See Fall Trees: Morton Arboretum

Morton Arboretum is a 30-minute drive from Chicago, this public garden and outdoor museum is the perfect place to let the kids run free while you relax and witness 4,200 types of trees change their colors to welcome fall.  Hiking trails, large sculptures, a Children’s Garden, and a toddler’s maze ensure that the whole family will be wholly occupied enjoying fall’s spectacular color display.

Related Post: A Weekend in Chicago: How to Make the Most of 2 Days

Where to Drink Wine: Cooper's Hawk Winery and Restaurant

An eight-minute drive from the Morton Arboretum Visitor Center will bring you to Cooper’s Hawk Winery and Restaurant, where you can toast the end of a perfect day with a crisp glass of wine and a well-balanced meal of meat, seafood, or vegetarian entrees. The kids’ menu also offers plenty of healthy satiating options!

arial view of soldier field at sunset

Moderately-Paced Itinerary

Where to Sleep: Hotel Versey

Hotel Versey is bright, trendy, casual hotel with a hip lobby full of board games. Located close to Lincoln Park.

Related Post: Top Attractions in Chicago, Illinois

Day One

Where to Go Biking: Chicago's Lakefront Neighborhoods Bike Tour

With Chicago’s Lakefront Neighborhoods Bike Tour you can ride past skyscrapers in Streeterville, luxury living in the Gold Coast, artists’ village in Old Town, and Lincoln Park. Recognized as a very excellent and very fun tour by National Geographic, USA Today, The Associated Press, Conde Nast Traveler, and more. All ages, all skill levels. Bring a windbreaker!

Where to Eat After Working Up An Appetite: Giordano's

Giordano’s is a casual Chicago chain renowned for its famous deep-dish pizza. They also serve salads, pasta, beer, and wine.

Where to Get a Sky View: Sky Deck Chicago

A 2-minute walk from Giordano’s is Sky Deck Chicago. Climb up to the 103rd floor of the former Sears Tower for clear observation boxes & views extending to four states. Beautiful panoramic photo opportunity!

Day Two

Where to Eat Breakfast: Salonica Restaurant

Salonica Restaurant is a Greek diner that serves a classic hearty breakfast that you’ll be very thankful for as you walk around the museum, an eight-minute walk away.

Related Post: How to Vacation in Chicago on a Budget

Where to Explore: Museum of Science and Industry

Museum of Science and Industry is the Western hemisphere’s largest science museum. Hands-on, interactive exhibits that are thoroughly engaging for kids and absolutely fascinating for adults. Life-sized submarines, WWII planes, Tesla Coil, a coal mine, a flight simulator, an IMAX theater, a mirror maze, a fairy castle. This museum has it all.

Where to Take an Afternoon Stroll: The Magnificent Mile

Head north over the Chicago River to get to Chicago’s premier commercial district, The Magnificent Mile. A vibrant, bustling street known for shops, bars, restaurants, and posh hotels, this street offers many excitements for both adults and kids. Build a doll version of yourself at the American Girl Place, visit the Disney® Store, or get some candy at Dylan’s Candy Bar. You can also admire views of the Chicago Water Tower, the Wrigley Building, and the John Hancock Center. 

Related Post: The Magnificent Mile Chicago: The Ultimate Guide Great Lakes Chicago

wide view of navy pier with the skyline in the background in Chicago, Illinois, USA

Day Three

Where to Grab Amazing Coffee: About Cocoa + Co. Coffee and Chocolate Café

Start the day with a cup of coffee or hot chocolate in the park. Head to About Cocoa + Co. Coffee and Chocolate Café at the south side of Lincoln Park. Grab a cup-to-go and begin your stroll through Chicago’s largest park.

Where to Enjoy Nature: Lincoln Park

Enjoy a delightful morning sipping a warm beverage as red maple, ash, birch, and elm trees put on a stunning display of colors above you. A free zoo, nature museum, a rowing house, and plenty of space to toss a football or flick a frisbee mean endless entertainment for active kids and hours of relaxing family time.

Related Post: Current Events and Festivals in Chicago, Illinois

Where to Eat Outdoors: Small Cheval Wells

Exit the park from the south entrance, near the Chicago History Museum, and walk south along Wells Street until you reach Small Cheval Wells, a local favorite with rustic patio seating. It won’t take long for everyone to decide what they want as there are only three options—burgers, fries, and shakes. A nine-minute drive, 20-minute walk, or a quick ride on the red line will bring you to your next stop.

Evening Adventure: Chicago Night Crime Tour

After a day of walking through the park, here’s an opportunity to rest your legs on a climate-controlled luxury bus for the Chicago Night Crime Tour. Infamous criminals and gangsters like Al Capone, John Dillinger, Terrible Tommy and famous crime scenes like the Biograph Theatre, Clark Street Bridge, Holy Name Cathedral are a few of the exciting stops on this 90-minute tour.

Action-Packed Adventure

Where to Sleep: Hotel Versey

Hotel Versey is a bright, trendy, casual hotel with a hip lobby full of board games. Located close to Lincoln Park.

Day One

Where to Go Biking: Chicago's Lakefront Neighborhoods Bike Tour

With Chicago’s Lakefront Neighborhoods Bike Tour you can ride past skyscrapers in Streetersville, luxury living in the Gold Coast, artists’ village in Old Town, and Lincoln Park. Recognized as a very excellent and very fun tour by National Geographic, USA Today, The Associated Press, Conde Nast Traveler, and more. All ages, all skill levels. Bring a windbreaker!

Where to Eat After Working Up An Appetite: Giordano's

Giordano’s is a casual Chicago chain renowned for its famous deep-dish pizza. They also serve salads, pasta, beer, and wine.

Related Post: 3 Days in Chicago: How to Make the Most of 72 Hours

Where to Get a Sky View: Sky Deck Chicago

A two-minute walk from Giordano’s is Sky Deck Chicago. Climb up to the 103rd floor of the former Sears Tower for clear observation boxes & views extending to four states. Beautiful panoramic photo opportunity!

Day Two

Where to Eat Breakfast: Salonica Restaurant

Salonica Restaurant is a Greek diner that serves a classic hearty breakfast that you’ll be very thankful for as you walk around the museum, an 8-minute walk away.

Where to Explore: Museum of Science and Industry

Museum of Science and Industry is the Western hemisphere’s largest science museum. Hands-on, interactive exhibits that are thoroughly engaging for kids and absolutely fascinating for adults. Life-sized submarines, WWII planes, Tesla Coil, a coal mine, a flight simulator, an IMAX theater, a mirror maze, a fairy castle. This museum has it all.

Where to Take an Afternoon Stroll: The Magnificent Mile

Head north over the Chicago River to get to Chicago’s premier commercial district, The Magnificent Mile. A vibrant, bustling street known for shops, bars, restaurants, and posh hotels, this street offers many excitements for both adults and kids. Build a doll version of yourself at the American Girl Place, visit the Disney Store, or get some candy at Dylan’s Candy Bar. You can also admire views of the Chicago Water Tower, the Wrigley Building, and the John Hancock Center.  

Day Three

Where to Grab Amazing Coffee: About Cocoa + Co. Coffee and Chocolate Café

Start the day with a cup of coffee or hot chocolate in the park. Head to About Cocoa + Co. Coffee and Chocolate Café at the south side of Lincoln Park. Grab a cup-to-go and begin your stroll through Chicago’s largest park.

Related Post: A Foodie’s Guide to Famous Chicago Restaurants

Where to Enjoy Nature: Lincoln Park

Enjoy a delightful morning sipping a warm beverage as red maple, ash, birch, and elm trees put on a stunning display of colors above you. A free zoo, nature museum, a rowing house, and plenty of space to toss a football or flick a frisbee mean endless entertainment for active kids and hours of relaxing family time.

Where to Eat Outdoors: Small Cheval Wells

Exit the park from the south entrance, near the Chicago History Museum, and walk south along Wells Street until you reach Small Cheval Wells, a local favorite with rustic patio seating. It won’t take long for everyone to decide what they want as there are only three options—burgers, fries, and shakes. A 9-minute drive, 20-minute walk, or a quick ride on the red line will bring you to your next stop.

Evening Adventure: Chicago Night Crime Tour

After a day of walking through the park, here’s an opportunity to rest your legs on a climate-controlled luxury bus for the Chicago Night Crime Tour. Infamous criminals and gangsters like Al Capone, John Dillinger, Terrible Tommy and famous crime scenes like the Biograph Theatre, Clark Street Bridge, Holy Name Cathedral are a few of the exciting stops on this 90-minute tour.

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