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2026

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2027

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2028

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Who is travelling?

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0
From
US $277 per person

City Break in Chicago Among Skyscrapers

4 days
Start and end in Chicago
4.2 (21 reviews)
From
US $277 per person

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

Select Date

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. 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
    Clark/Lake Blue Line Station
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  2. Day 2

    Chicago

    Chicago
    Accommodation
    Hotel (Central Loop Hotel)

    Optional Activities

    • Willis Tower (Skydeck Chicago) - Glass-bottomed Ledge experience
    • Historic Begin Route 66 Sign
    • Cloud Gate ('The Bean')
    • Tribune Tower
    • John Hancock Tower (360 Chicago) - including 'Tilt' experience
    Landmarks
    Willis Tower (Skydeck Chicago)
    Route 66 Start Marker
    Cloud Gate ('The Bean')
    Tribune Tower
    John Hancock Tower (875 North Michigan Avenue)
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  3. Day 3

    Chicago

    Chicago
    Accommodation
    Hotel (Central Loop Hotel)

    Optional Activities

    • Elevated Train Ride through the Loop on Brown Line
    • Chicago Loop Architectural Walk
    • Sullivan Center on State Street
    • McCormick Bridgehouse & Chicago River Museum
    • Guided Architectural Walking Tour with Chicago Architecture Center
    Landmarks
    Merchandise Mart
    First Skyscraper Site (La Salle and Adams Street)
    Monadnock Building
    Sullivan Center
    McCormick Bridgehouse & Chicago River Museum
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  4. Day 4

    Chicago

    Chicago

    Optional Activities

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

Want to read it later?

Download this tour’s PDF brochure and start tour planning offline

What's Included

Expand All
  • 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
4.2 (21 reviews)
Response time
within 1 day
Response rate
100%
Cancellation policy

Reviews from other tours by Worldee

  • Peter5.0February 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 & Availability

Select departure month and travellers

Select Date

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 on 26 Aug, 2026
  • Instant Confirmation
    From Thursday
    27 Aug, 2026
    To Sunday
    30 Aug, 2026
    English
    From:
    US$878 per person
    Price based on Shared Room
  • Instant Confirmation
    From Friday
    28 Aug, 2026
    To Monday
    31 Aug, 2026
    English
    From:
    US$882 per person
    Price based on Shared Room
  • Instant Confirmation
    From Saturday
    29 Aug, 2026
    To Tuesday
    1 Sep, 2026
    English
    From:
    US$579 per person
    Price based on Shared Room
  • Instant Confirmation
    From Sunday
    30 Aug, 2026
    To Wednesday
    2 Sep, 2026
    English
    From:
    US$533 per person
    Price based on Shared Room
  • Instant Confirmation
    From Monday
    31 Aug, 2026
    To Thursday
    3 Sep, 2026
    English
    From:
    US$596 per person
    Price based on Shared Room
  • Instant Confirmation
    From Tuesday
    1 Sep, 2026
    To Friday
    4 Sep, 2026
    English
    From:
    US$508 per person
    Price based on Shared Room
  • Instant Confirmation
    From Wednesday
    2 Sep, 2026
    To Saturday
    5 Sep, 2026
    English
    From:
    US$531 per person
    Price based on Shared Room
  • Instant Confirmation
    From Thursday
    3 Sep, 2026
    To Sunday
    6 Sep, 2026
    English
    From:
    US$576 per person
    Price based on Shared Room
  • Instant Confirmation
    From Friday
    4 Sep, 2026
    To Monday
    7 Sep, 2026
    English
    From:
    US$533 per person
    Price based on Shared Room
  • Instant Confirmation
    From Saturday
    5 Sep, 2026
    To Tuesday
    8 Sep, 2026
    English
    From:
    US$526 per person
    Price based on Shared Room

Want to read it later?

Download this tour’s PDF brochure and start tour planning offline

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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 $277 per person

Price based on Cheapest Room

Price based on Shared Room

Price based on Private Single Room

Price based on Private Double Room

Select Date

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:

Earn while you share

With TourRadar RISE, you can earn commission when someone books a tour through a link you share — like this one.

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 November 22nd, 2026 a full payment is necessary. For tours departing after November 22nd, 2026, 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
  • 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