31 Dec, 2023 - 06 Jan, 2024

7 Days trip in Chicago, Illinois, United States

500 - 2500 USD Beaches Food exploration Nightlife City sightseeing Shopping

Chicago is a vibrant metropolis known for its stunning architecture, world-class museums, and delicious deep-dish pizza.

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Washington
UTC-10:00
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☁️ 29.76°C
Bus
Train
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Itinerary

Sun,31 Dec
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  1. 1
    Chicago

    Millennium Park

    Visit Millennium Park to see The Bean and take a photo of the iconic sculpture, enjoy a picnic in the park

  2. 2
    Chicago

    Magnificent Mile

    Shop at high-end department stores and designer boutiques

  3. 4
    Chicago

    The Green Mill Cocktail Lounge

    Listen to jazz music at this historic speakeasy

  4. 5
    Chicago

    Alinea

    Experience cutting-edge cuisine at this three-Michelin-starred restaurant

Mon,01 Jan
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  1. 6
    Chicago

    Art Institute of Chicago

    View iconic works of art, including American Gothic and Nighthawks

  2. 7
    Chicago

    Chicago Riverwalk

    Take a stroll along the Chicago River and admire the architecture

  3. 8
    Chicago

    Chicago Style Pizza

    Indulge in a deep-dish pizza from a local pizzeria

  4. 9
    Chicago

    Chicago Theatre

    See a Broadway show at this historic theater

  5. 10
    Chicago

    The Violet Hour

    Enjoy artisanal cocktails in a swanky speakeasy atmosphere

Tue,02 Jan
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  1. 11
    Chicago

    Lincoln Park Zoo

    Visit the free zoo and see animals from around the world

  2. 12
    Chicago

    Chicago Botanic Garden

    Explore the gardens and see 27 different display gardens

  3. 13
    Chicago

    River North Gallery District

    See contemporary art in this vibrant neighborhood

  4. 14
    Chicago

    Second City

    Laugh at improv and sketch comedy at the famous Second City theater

Wed,03 Jan
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  1. 15
    Chicago

    Oak Street Beach

    Soak up the sun at one of Chicago's beaches

  2. 16
    Chicago

    Chicago History Museum

    Learn about Chicago's history and culture

  3. 17
    Chicago

    Lincoln Square

    Shop at independent stores and boutiques in this charming neighborhood

  4. 18
    Chicago

    The Signature Lounge at the 96th

    Sip a cocktail and enjoy the view of the skyline from the 96th floor of the John Hancock Center

Thu,04 Jan
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  1. 19
    Chicago

    Chicago Architecture Center

    Learn about Chicago's architecture and take a boat tour along the Chicago River

  2. 20
    Chicago

    Chicago Cultural Center

    Visit the free cultural center and see art exhibits, performances, and events

  3. 21
    Chicago

    Wrigley Field

    Take a guided tour of the iconic ballpark

  4. 22
    Chicago

    King Crab House

    Savor fresh seafood at this popular spot

  5. 23
    Chicago

    Untitled Supper Club

    Listen to live music and enjoy cocktails in a vintage-inspired speakeasy

Fri,05 Jan
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  1. 24
    Chicago

    Museum of Science and Industry

    Interact with exhibits that explore science and technology

  2. 25
    Chicago

    Chicago Riverwalk

    Take a riverboat cruise along the Chicago River

  3. 26
    Chicago

    West Loop

    Sample creative cuisine at some of the city's top restaurants

  4. 27
    Chicago

    Buddy Guy's Legends

    Listen to blues music at this legendary club

Sat,06 Jan
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  1. 28
    Chicago

    Garfield Park Conservatory

    View exotic plants from around the world in this free conservatory

  2. 29
    Chicago

    Chinatown

    Shop for souvenirs and try dim sum at a local eatery

  3. 30
    Chicago

    Chicago Riverwalk

    Have dinner at a restaurant overlooking the Chicago River

  4. 31
    Chicago

    The Second City

    Laugh at improv and sketch comedy at the famous Second City theater

Estimated Cost (USD)

Accommodation

Hotel
150-300
Airbnb
100-250
Hostel
20-50
Bed and Breakfast
100-200
Luxury Hotel
300-1000

Transportation

Public Transit
25
Taxi
40-100
Uber/Lyft
30-100
Car Rental
50-100 per day
Bike Rental
15-30 per day

Food

Budget Eats
5-15
Street Food
5-10
Gourmet Food
30-100
Drinks at a Bar
5-15
Fine Dining
100-300

Activities

Museums
10-25
Sightseeing Tours
30-100
Concerts/Shows
50-200
Sports Events
50-200
Shopping
100-500