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2026

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2027

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Jul
Aug
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2028

Jan
Feb
Mar
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Who is travelling?

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0
From
US $268 per person

City Break in Chicago Among Skyscrapers

4 days
•
Start and end in Chicago
4.1 (25 reviews)
From
US $268 per person
+ $713 Studio Apartment with King Bed

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

Booking needs min. 2 travelers

Select departure month

Select departure month

2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0

Best price guarantee Learn More

Plan your adventure:
City & Culture
Immerse yourself in rich history and local traditions
Self-guided
Independent exploration, backed by expert advice and support
Low Intensity
Travelers can expect some light physical activities
Guided in English
All Ages Welcome

Itinerary

  1. Intro

    Introduction

  2. Day 1

    Chicago

    Chicago
    Accommodation
    Hotel (Central Loop Hotel)

    Optional Activities

    • Arrival and Metro Ride from O'Hare
    • Exploring the Chicago Riverwalk
    Landmarks
    Chicago Riverwalk
    O'Hare International Airport
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  3. Day 2

    Chicago

    Chicago
    Accommodation
    Hotel (Central Loop Hotel)

    Optional Activities

    • Willis Tower (Skydeck Chicago)
    • Historic Begin Route 66 Sign
    • Cloud Gate ('The Bean')
    • Tribune Tower
    • John Hancock Tower (360 Chicago)
    Landmarks
    Willis Tower
    Route 66 Starting Point
    Cloud Gate
    Tribune Tower
    John Hancock Tower
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  4. Day 3

    Chicago

    Chicago
    Accommodation
    Hotel (Central Loop Hotel)

    Optional Activities

    • Elevated Train Ride through the Loop
    • Chicago Loop Architectural Walk
    • Sullivan Center on State Street
    • McCormick Bridgehouse & Chicago River Museum
    • Guided Architectural Walking Tour
    Landmarks
    Merchandise Mart
    The Loop (Elevated Train System)
    Monadnock Building
    Sullivan Center
    McCormick Bridgehouse & Chicago River Museum
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  5. Day 4

    Chicago

    Chicago

    Optional Activities

    • Chicago Riverwalk Revisited
    • Souvenir Shopping
    • Lakeside Walk
    • Final Elevated Train Ride
    Landmarks
    Chicago Riverwalk
    Lake Michigan
    O'Hare International Airport
    Itinerary Image 1

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What's Included

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  • Accommodation
  • Guide
  • Meals
  • Additional Services

What's Not Included

  • Flights
  • Additional Services

Where You'll Stay

All accommodations are subject to change

Operated by

Worldee

Rating
4.1 (25 reviews)
Response time
within 1 day
Response rate
96%
Cancellation policy
Learn more

Reviews from other tours by Worldee

  • Peter5.0•February 2026
    Booked a Las Vegas trip by Worldee. Everything worked as expected, no issues at all. The plan was clear and the trip...
    Show more

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Dates & Prices

Select departure month

Select departure month

2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0
Upcoming departures
Hurry, deals only available for a limited time!
Ends in2d2h12m27s
  • From Saturday
    10 Oct, 2026
    To Tuesday
    13 Oct, 2026
    English
    From:
    US$712 per person
    Price based on Private Double Room
    Studio Apartment with King Bed
    $713
  • From Sunday
    11 Oct, 2026
    To Wednesday
    14 Oct, 2026
    English
    From:
    US$712 per person
    Price based on Private Double Room
    Studio Apartment with King Bed
    $713
  • Instant Confirmation
    From Monday
    12 Oct, 2026
    To Thursday
    15 Oct, 2026
    English
    From:
    US$712 per person
    Price based on Private Double Room
    Studio Apartment with King Bed
    $713
  • Instant Confirmation
    From Tuesday
    13 Oct, 2026
    To Friday
    16 Oct, 2026
    English
    From:
    US$712 per person
    Price based on Private Double Room
    Studio Apartment with King Bed
    $713
  • Instant Confirmation
    From Wednesday
    14 Oct, 2026
    To Saturday
    17 Oct, 2026
    English
    From:
    US$708 per person
    Price based on Private Double Room
    Club Room
    $709
  • Instant Confirmation
    From Thursday
    15 Oct, 2026
    To Sunday
    18 Oct, 2026
    English
    From:
    US$712 per person
    Price based on Private Double Room
    Studio Apartment with King Bed
    $713
  • Instant Confirmation
    From Friday
    16 Oct, 2026
    To Monday
    19 Oct, 2026
    English
    From:
    US$712 per person
    Price based on Private Double Room
    Studio Apartment with King Bed
    $713
  • Instant Confirmation
    From Saturday
    17 Oct, 2026
    To Tuesday
    20 Oct, 2026
    English
    From:
    US$712 per person
    Price based on Private Double Room
    Studio Apartment with King Bed
    $713
  • Instant Confirmation
    From Sunday
    18 Oct, 2026
    To Wednesday
    21 Oct, 2026
    English
    From:
    US$712 per person
    Price based on Private Double Room
    Studio Apartment with King Bed
    $713
  • Instant Confirmation
    From Monday
    19 Oct, 2026
    To Thursday
    22 Oct, 2026
    English
    From:
    US$712 per person
    Price based on Private Double Room
    Studio Apartment with King Bed
    $713

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More benefits
Can’t find the answer to your question?
Reach out to the experts at Worldee with your enquiry, they usually respond within 1 day.
From
US $268 per person
+ $713 Studio Apartment with King Bed

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

Booking needs min. 2 travelers

Select departure month

Select departure month

2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0

Best price guarantee Learn More

Plan your adventure:

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Good to Know

Tour ID: 364434

  • Currency
    $
    US Dollar
    USA
  • Plugs & Adapters

    As a traveler from England, Australia, New Zealand, South Africa you will need an adaptor for types A, B.

    Type A
    USA
    Type B
    USA
  • Visa
    • Unfortunately we cannot offer you a visa application service. Whether you need a visa or not depends on your nationality and where you wish to travel. Assuming your home country does not have a visa agreement with the country you're planning to visit, you will need to apply for a visa in advance of your scheduled departure.
    • Here is an indication for which countries you might need a visa. Please contact the local embassy for help applying for visas to these places.
  • Payment information
    • For any tour departing before January 7th, 2027 a full payment is necessary. For tours departing after January 7th, 2027, a minimum payment of 40% is required to confirm your booking with Worldee. The final payment will be automatically charged to your credit card on the designated due date. The final payment of the remaining balance is required at least 95 days prior to the departure date of your tour. TourRadar never charges you a booking fee and will charge you in the stated currency.
    • Some departure dates and prices may vary and Worldee will contact you with any discrepancies before your booking is confirmed.
    • The following cards are accepted for "Worldee" tours: Visa, Maestro, Mastercard, American Express or PayPal. TourRadar does NOT charge you an extra fee for using any of these payment methods.
  • Cancellation Policy
    • Cancellation terms may vary per tour. Please check for the full cancellation policy here.

      Checking the cancellation terms for this tour…
    • Your money is protected.
      TourRadar is an authorized agent of Worldee, and we handle payments so you don't have to. Payment is securely transferred to the Operator based on your departure date.
  • Insurance

    Our travel protection from our award-winning partner, XCover, means you and your travel companions can book with peace of mind knowing there’s protection available in case your trip doesn’t go to plan. At checkout you will be able to select between different options in case you or the tour are eligible for insurance. In case no option is available, you are always able to purchase travel insurance outside of TourRadar.

    Checking which travel protection options are available for you…
  • Accessibility
    Some tours are not suitable for mobility-restricted traveler, however, some operators may be able to accommodate special requests. For any enquiries, you can contact our customer support team, who are ready and waiting to help you.

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0

Select departure month

2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec