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Windy City Escape: 4-Day Solo Adventure in Chicago

4.7
143

Excellent 143 reviews

clock Duration : 

4D/3N

About

This is the 3 nights and 4 days solo package to Chicago, one of the best combinations of city tour and self-discovery. The city has great architecture, an exciting history, and a vibrant arts culture, making it perfect for a solicitor's visit. 

Spend a day visiting some of the big sites, such as the Willis Tower, and one or two of the large museums in the city and the Art In...

Itinerary

Day 1

Arrival in Chicago & Millennium Park

  • New York to Chicago
  • Dinner
  • Airport to Hotel
  • Stay Included

  • Take a flight from New York to reach Chicago O'Hare International Airport Flight. 
  • Get comfortable private transfer to your hotel for check-in to the "The Langham Chicago." 
  • Once settled, take a short walk to Millennium Park, which contains the famous Cloud Gate and the Bean-and Crown Fountain. 
  • Spend an afternoon strolling in Grant Park, "Chicago's front yard," which boasts beautiful gardens, lovely walking paths, and the grand Buckingham Fountain. 
  • Back to your hotel for a quiet evening gazing out over the city or dining out at one of Chicago's best restaurants. 

Day 2

Go on Architecture Tour & Chicago Riverwalk

  • Breakfast

  • Take an architectural boat tour of the Chicago River after breakfast and find the main skyscrapers that are well-known and some of its historic buildings. 
  • Witness the view of the city from a height of 1,353 feet at Willis Tower Skydeck. 
  • Have lunch at one of the many charming cafes along the Chicago Riverwalk, a bustling pedestrian thoroughfare with shops, restaurants, and pictures-postcard views. 
  • Now, in the afternoon visit Chicago Cultural Center, famous for excellent architecture and gratis exhibitions. 
  • The evening beckons to visit the energetic nightlife of Chicago or have some of the world's best deep-dish pizzas at Lou Malnati's Pizzeria. 

Day 3

Visit Museums & The Art Institute of Chicago

  • Breakfast

  • After breakfast, spend the day exploring Chicago's great museums and visit the Art Institute of Chicago, as it has an incredible Impressionist and Post-Impressionist collection. 
  • Walk over to the next Museum Campus, the Field Museum of Natural History, and the Shedd Aquarium. 
  • Extra free time for an afternoon visit to Navy Pier, which features rides and attractions as well as the great Ferris wheel view over Lake Michigan. 
  • Get back to your hotel for a rest or some good old-fashioned high-end shopping, take a stroll down Michigan Avenue (The Magnificent Mile). 

Day 4

Explore Wicker Park & Departure from Chicago

  • Chicago to New York
  • Breakfast
  • Hotel to Airport

  • In the morning, stroll around Wicker Park. It is a very beautiful, cool place with special stores, coffee shops, and street art. 
  • Sit for a while in one of the neighborhood green spaces or grab brunch at a local café before returning to work. 
  • Get a private ride to O'Hare International Airport in order to take the return flight to New York. 

  • Transfer
  • Dinner as per Itinerary
  • Stay Included
  • Flight
  • Stroll through Millennium Park and enjoy sights like Cloud Gate and Buckingham Fountain.
  • Enjoy panoramic views of the city from the Willis Tower Skydeck and take a stroll along the Chicago Riverwalk.
  • Visit the Art Institute of Chicago, which has world-renowned Impressionist and Post-Impressionist works.
  • Take a Chicago architecture boat tour down the Chicago River and see this city's internationally famous skyline.
  • Visit the blooming neighborhood of Wicker Park, which is full of fine art and local boutique shopping.
  • Explore the Field Museum of Natural History and the Shedd Aquarium, situated on Chicago's iconic Museum Campus.
  • Taste live flavors of the city, but mostly, it is great deep-dish pizza.

Hotels

Day 1-2-3

Chicago

The Langham Chicago

  • Roundtrip airfare from and to New York 
  • Private arrival and departure airport transfer 
  • Accommodation at "The Langham Chicago": 03 nights 
  • Architecture boat tour of the Chicago River 
  • Admission to Willis Tower Skydeck, the Art Institute of Chicago, and the Field Museum
  • Guided tours and entry fees to all listed museums and attractions  
  • Breakfast: "03" 
  • Dinner: "01" 
  • Travel Insurance 

Hotel included in package:

Starting from:

$2000 $2400

per adult on twin sharing

Destination covered

Chicago

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Chicago Package for 3 nights and 4 days : Frequently asked questions

Yes, it's perfect for solo travelers, whether new to Chicago or returning.

The ideal time is between May and September for pleasant weather and outdoor activities.

Yes, the package can be tailored to include additional activities.

Pack comfortable walking shoes, layers for variable weather, and a camera for capturing moments.