Christmas in Chicago
Welcome to an exhilarating journey through the Windy City! In this 5-day Chicago itinerary, we'll explore the best hotels, restaurants, famous landmarks, off-the-beaten-path experiences, and enchanting Christmas activities that make the city shine during the holiday season. Get ready for a memorable and magical adventure.
24 Places • 2 Saves • ago
Free

Day 1: Downtown Delights

Hotel: Check-in at the Palmer House, a Hilton Hotel, where you'll experience classic Chicago luxury.

Palmer House a Hilton Hotel
@VividVoyagers
Add to
Details

Breakfast: Kickstart your day with a scrumptious breakfast at Wildberry Pancakes & Cafe.

Wildberry Pancakes & Cafe
@VividVoyagers
Add to
Details

Activity 1: Visit the iconic Millennium Park, where you'll find the "Bean" (Cloud Gate) and enjoy the winter ice skating rink.

Millennium Park
@VividVoyagers
Add to
Details

Activity 2: Stroll along the Magnificent Mile, decked out in festive lights and window displays, for some Christmas shopping.

Magnificent Mile
@VividVoyagers
Add to
Details

Dinner: Dine at The Gage, offering a mix of traditional and modern American cuisine.

Add to
Details

Day 2: Art and Culture Exploration

Hotel: Spend your second night at the historic Chicago Athletic Association Hotel.

Chicago Athletic Association - The Unbound Collection by Hyatt
@VividVoyagers
Add to
Details

Breakfast: Enjoy a hearty breakfast at The Allis, an elegant dining spot within the hotel.

The Allis Chicago
@VividVoyagers
Add to
Details

Activity 1: Visit the Art Institute of Chicago to explore world-class art collections, including Grant Wood's "American Gothic."

The Art Institute of Chicago
@VividVoyagers
Add to
Details

Activity 2: Head to the Chicago Cultural Center, marvel at the breathtaking Tiffany glass dome, and check out rotating art exhibitions.

Chicago Cultural Center
@VividVoyagers
Add to
Details

Dinner: Savor an Italian feast at The Purple Pig, a renowned Chicago eatery.

The Purple Pig Restaurant
@VividVoyagers
Add to
Details

Day 3: Hidden Gems and Riverside Views

Hotel: Stay at the sleek and stylish London House Chicago, Curio Collection by Hilton.

London House
@VividVoyagers
Add to
Details

Breakfast: Start your day with a scenic breakfast at LH on 21, offering breathtaking river and city views.

LH Rooftop
@VividVoyagers
Add to
Details

Activity 1: Explore the Chicago Riverwalk, a serene and less touristy gem.

Add to
Details

Activity 2: Tour the Money Museum at the Federal Reserve Bank of Chicago for an educational and unique experience.

Chicago Fed Money Museum
@VividVoyagers
Add to
Details

Dinner: Enjoy Chicago-style deep-dish pizza at Lou Malnati's Pizzeria.

Lou Malnati's Pizzeria
@VividVoyagers
Add to
Details

  Day 4: Christmas Charm and Local Flavor

Hotel: Spend your fourth night at The Drake, a Hilton Hotel, famous for its festive holiday decor.

Add to
Details

Breakfast: Experience a classic Chicago breakfast at Yolk.

Yolk - Marina City
@VividVoyagers
Add to
Details

Activity 1: Immerse yourself in Christmas magic at the Christkindlmarket, a traditional German holiday market.

Christkindlmarket Chicago
@VividVoyagers
Add to
Details

Activity 2: Take a walk around Lincoln Park ZooLights, an enchanting display of holiday lights and seasonal activities.

Lincoln Park Zoo
@VividVoyagers
Add to
Details

Dinner: Savor a Chicago hot dog at Portillo's.

Portillo's & Barnelli's Chicago
@VividVoyagers
Add to
Details

  Day 5: Lakefront Beauty and Farewell

Breakfast: Wrap up your trip with a leisurely breakfast at Original Pancake House.

The Original Pancake House
@VividVoyagers
Add to
Details

Activity 1: Visit the Navy Pier, decorated for the season and offering various attractions.

Add to
Details

Activity 2: Explore the Chicago Lakefront Trail for stunning views of Lake Michigan and the city skyline.

Lakefront Trail
@VividVoyagers
Add to
Details

Lunch: Enjoy a farewell lunch at the Chicago Classic, Garrett Popcorn Shops.

Garrett Popcorn Shops
@VividVoyagers
Add to
Details

End your 5-day Chicago adventure on a high note, taking with you unforgettable memories of iconic landmarks, hidden treasures, and the enchanting spirit of Christmas in this magnificent city!

* * *
CURATED BY
Traveling around the globe, sharing handpicked destinations, hidden gems, and must-see landmarks! Next stops - 📍Coronado Island 📍Italy
Send A Tip
Support Vivid Voyagers’s work.
Select your tip amount
$5
$10
$20
$50
Or type in other amount
Powered by Thatch
The home for unique & authentic travel
Powered by Thatch: Where great trips are made.
© Vivid Voyagers Privacy Terms
Christmas in Chicago
Welcome to an exhilarating journey through the Windy City! In this 5-day Chicago itinerary, we'll explore the best hotels, restaurants, famous landmarks, off-the-beaten-path experiences, and enchanting Christmas activities that make the city shine during the holiday season. Get ready for a memorable and magical adventure.
24 Places • 2 Saves • ago
Free

Day 1: Downtown Delights

Hotel: Check-in at the Palmer House, a Hilton Hotel, where you'll experience classic Chicago luxury.

Palmer House a Hilton Hotel
@VividVoyagers
Add to
Details

Breakfast: Kickstart your day with a scrumptious breakfast at Wildberry Pancakes & Cafe.

Wildberry Pancakes & Cafe
@VividVoyagers
Add to
Details

Activity 1: Visit the iconic Millennium Park, where you'll find the "Bean" (Cloud Gate) and enjoy the winter ice skating rink.

Millennium Park
@VividVoyagers
Add to
Details

Activity 2: Stroll along the Magnificent Mile, decked out in festive lights and window displays, for some Christmas shopping.

Magnificent Mile
@VividVoyagers
Add to
Details

Dinner: Dine at The Gage, offering a mix of traditional and modern American cuisine.

Add to
Details

Day 2: Art and Culture Exploration

Hotel: Spend your second night at the historic Chicago Athletic Association Hotel.

Chicago Athletic Association - The Unbound Collection by Hyatt
@VividVoyagers
Add to
Details

Breakfast: Enjoy a hearty breakfast at The Allis, an elegant dining spot within the hotel.

The Allis Chicago
@VividVoyagers
Add to
Details

Activity 1: Visit the Art Institute of Chicago to explore world-class art collections, including Grant Wood's "American Gothic."

The Art Institute of Chicago
@VividVoyagers
Add to
Details

Activity 2: Head to the Chicago Cultural Center, marvel at the breathtaking Tiffany glass dome, and check out rotating art exhibitions.

Chicago Cultural Center
@VividVoyagers
Add to
Details

Dinner: Savor an Italian feast at The Purple Pig, a renowned Chicago eatery.

The Purple Pig Restaurant
@VividVoyagers
Add to
Details

Day 3: Hidden Gems and Riverside Views

Hotel: Stay at the sleek and stylish London House Chicago, Curio Collection by Hilton.

London House
@VividVoyagers
Add to
Details

Breakfast: Start your day with a scenic breakfast at LH on 21, offering breathtaking river and city views.

LH Rooftop
@VividVoyagers
Add to
Details

Activity 1: Explore the Chicago Riverwalk, a serene and less touristy gem.

Add to
Details

Activity 2: Tour the Money Museum at the Federal Reserve Bank of Chicago for an educational and unique experience.

Chicago Fed Money Museum
@VividVoyagers
Add to
Details

Dinner: Enjoy Chicago-style deep-dish pizza at Lou Malnati's Pizzeria.

Lou Malnati's Pizzeria
@VividVoyagers
Add to
Details

  Day 4: Christmas Charm and Local Flavor

Hotel: Spend your fourth night at The Drake, a Hilton Hotel, famous for its festive holiday decor.

Add to
Details

Breakfast: Experience a classic Chicago breakfast at Yolk.

Yolk - Marina City
@VividVoyagers
Add to
Details

Activity 1: Immerse yourself in Christmas magic at the Christkindlmarket, a traditional German holiday market.

Christkindlmarket Chicago
@VividVoyagers
Add to
Details

Activity 2: Take a walk around Lincoln Park ZooLights, an enchanting display of holiday lights and seasonal activities.

Lincoln Park Zoo
@VividVoyagers
Add to
Details

Dinner: Savor a Chicago hot dog at Portillo's.

Portillo's & Barnelli's Chicago
@VividVoyagers
Add to
Details

  Day 5: Lakefront Beauty and Farewell

Breakfast: Wrap up your trip with a leisurely breakfast at Original Pancake House.

The Original Pancake House
@VividVoyagers
Add to
Details

Activity 1: Visit the Navy Pier, decorated for the season and offering various attractions.

Add to
Details

Activity 2: Explore the Chicago Lakefront Trail for stunning views of Lake Michigan and the city skyline.

Lakefront Trail
@VividVoyagers
Add to
Details

Lunch: Enjoy a farewell lunch at the Chicago Classic, Garrett Popcorn Shops.

Garrett Popcorn Shops
@VividVoyagers
Add to
Details

End your 5-day Chicago adventure on a high note, taking with you unforgettable memories of iconic landmarks, hidden treasures, and the enchanting spirit of Christmas in this magnificent city!

* * *
CURATED BY
Traveling around the globe, sharing handpicked destinations, hidden gems, and must-see landmarks! Next stops - 📍Coronado Island 📍Italy
Send A Tip
Support Vivid Voyagers’s work.
Select your tip amount
$5
$10
$20
$50
Or type in other amount
Powered by Thatch
The home for unique & authentic travel
Powered by Thatch: Where great trips are made.
© Vivid Voyagers Privacy Terms