Where?
When?
2

Where to?

Traveling when?

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

Who is travelling?

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0
From
$757
US $643 per person

Chicago - The Home of Skyscrapers

7 days
•
Start and end in Chicago
4.2 (1 review)
From
$757
15% off
US $643 per person
+ $3,481 additional upfront costs

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
Pay only 40% today. The rest is due 95 days before departure. Learn more

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

Explore our featured adventures

TourRadar earns higher commission on featured adventures here.

Itinerary

  1. Intro

    Introduction

  2. Day 1

    Chicago

    Chicago
    Accommodation
    Hotel (Arlo Chicago)

    Optional Activities

    • Stroll along the Chicago Riverwalk
    Landmarks
    O'Hare Airport
    Clark/Lake Station
    Chicago Riverwalk
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  3. Day 2

    Chicago

    Chicago
    Accommodation
    Hotel (Arlo Chicago)

    Optional Activities

    • Step onto the glass terraces of Willis Tower Skydeck, perched 412 meters above the city
    • Discover the start of America's iconic Route 66 on Adams Street
    • Marvel at Cloud Gate, affectionately known as 'The Bean'
    • Admire the neo-Gothic Tribune Tower
    • Experience the 'Tilt' at John Hancock Tower (360 Chicago) with an evening drink
    Landmarks
    Willis Tower Skydeck
    Route 66 Historic Sign
    Cloud Gate
    Tribune Tower
    John Hancock Tower (360 Chicago)
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  4. Day 3

    Chicago

    Chicago
    Accommodation
    Hotel (Arlo Chicago)

    Optional Activities

    • Enjoy a scenic ride on the Elevated Brown Line
    • Wander through the streets of the Chicago Loop
    • Visit the significant corner of La Salle and Adams Street, site of the world's first steel-framed skyscraper
    • Admire the grandeur of the Monadnock Building on Jackson Boulevard
    • Explore the magnificent Sullivan Center (Target on State Street)
    Landmarks
    Brown Line (Elevated Train)
    Chicago Loop
    La Salle and Adams Street
    Monadnock Building
    Sullivan Center (Target on State Street)
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  5. Day 4

    Chicago

    Chicago
    Accommodation
    Hotel (Arlo Chicago)

    Optional Activities

    • Immerse yourself in scientific discovery and historical innovation at the Museum of Science and Industry
    • Explore world-class collections and masterpieces at the Art Institute of Chicago
    Landmarks
    Museum of Science and Industry
    Art Institute of Chicago
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  6. Day 5

    Chicago

    Chicago
    Accommodation
    Hotel (Arlo Chicago)

    Optional Activities

    • Uncover the fascinating and sometimes graphic history of medicine at the International Museum of Surgical Science
    • Delve into the engineering marvels of Chicago's famous movable bridges at the McCormick Bridgehouse & Chicago River Museum
    Landmarks
    International Museum of Surgical Science
    McCormick Bridgehouse & Chicago River Museum
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  7. Day 6

    Chicago

    Chicago
    Accommodation
    Hotel (Arlo Chicago)

    Optional Activities

    • Take a leisurely stroll through the dynamic Chicago Loop
    • Find a peaceful spot along the scenic Chicago Riverwalk to reflect on your journey
    • Walk along the picturesque Lake Michigan shoreline
    Landmarks
    Chicago Loop
    Chicago Riverwalk
    Lake Michigan
    Itinerary Image 1Itinerary Image 2Itinerary Image 3
  8. Day 7

    Chicago to O'Hare Airport

    Chicago to O'Hare Airport
    Meals
    Breakfast
    Landmarks
    Chicago Riverwalk
    O'Hare Airport
    Itinerary Image 1Itinerary Image 2Itinerary Image 3

Want to read it later?

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

What's Included

Expand All
  • Accommodation
  • Guide
  • Additional Services

What's Not Included

  • Flights

Where You'll Stay

All accommodations are subject to change

Operated by

Worldee

Rating
4.1 (26 reviews)
Response time
within 1 day
Response rate
100%
Cancellation policy
Learn more

Traveler Reviews

4.2
Overall rating based on 1 Reviews

Sort by

Most recent
Most popular
Highest first
Lowest first

Sort by

Most Recent
Most Popular
Highest First
Lowest First
  • Philip
    Philip4.2•October 2026
    The itinerary is off-the-beaten path. The location of the hotel is superb; close (almost) to everything in the...
    Show more
    Traveled in September 2026
    Reply from: Worldee
    Thank you for your review! We’re very happy to hear that you enjoyed the trip and had a great adventure. We really appreciate your feedback and will take it into consideration for our future trips. We hope to travel with you again someday! 😊
    Show more

Sign up or log in to access your TourRadar+ savings

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 on 14 Oct, 2026
  • Instant Confirmation
    From Friday
    16 Oct, 2026
    To Thursday
    22 Oct, 2026
    English
    From:
    US$1,628 per person
    Price based on Private Double Room
    Additional Upfront
    $3,481
  • Instant Confirmation
    From Saturday
    17 Oct, 2026
    To Friday
    23 Oct, 2026
    English
    From:
    US$3,583 per person
    Price based on Private Double Room
    Classic room with a King bed
    $3,583
  • Instant Confirmation
    From Sunday
    18 Oct, 2026
    To Saturday
    24 Oct, 2026
    English
    From:
    US$3,583 per person
    Price based on Private Double Room
    Classic room with a King bed
    $3,583
  • Instant Confirmation
    From Monday
    19 Oct, 2026
    To Sunday
    25 Oct, 2026
    English
    From:
    US$3,583 per person
    Price based on Private Double Room
    Classic room with a King bed
    $3,583
  • Instant Confirmation
    From Tuesday
    20 Oct, 2026
    To Monday
    26 Oct, 2026
    English
    From:
    US$1,628 per person
    Price based on Private Double Room
    King
    $1,628
  • Instant Confirmation
    From Wednesday
    21 Oct, 2026
    To Tuesday
    27 Oct, 2026
    English
    From:
    US$3,040 per person
    Price based on Private Double Room
    Accommodation with 2 Queen beds
    $3,040
  • Instant Confirmation
    From Thursday
    22 Oct, 2026
    To Wednesday
    28 Oct, 2026
    English
    From:
    US$2,948 per person
    Price based on Private Double Room
    Accommodation with 2 Queen beds
    $2,948
  • Instant Confirmation
    From Friday
    23 Oct, 2026
    To Thursday
    29 Oct, 2026
    English
    From:
    US$3,020 per person
    Price based on Private Double Room
    Accommodation with 2 Queen beds
    $3,020
  • Instant Confirmation
    From Saturday
    24 Oct, 2026
    To Friday
    30 Oct, 2026
    English
    From:
    US$2,855 per person
    Price based on Private Double Room
    Accommodation with 2 Queen beds
    $2,855
  • Instant Confirmation
    From Sunday
    25 Oct, 2026
    To Saturday
    31 Oct, 2026
    English
    From:
    US$1,854 per person
    Price based on Private Double Room
    Standard Room with Queen Bed
    $1,854

Want to read it later?

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

Why book with TourRadar?

    • Trusted and vetted operators
    • Rated excellent on
    • Best price guarantee
    • 24/7 customer support
    • Unlock exclusive TourRadar+ member savings

    To protect your payment and ensure your booking will be processed in United States, never transfer or communicate outside of the TourRadar website or app.

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.

Trip essentials

Good to know

Tour ID: 319603

The practical details for your trip across USA: money, plugs and flexible ways to pay, all in one place.

Have a question? Chat with a travel expert

  • Pay in installments

    Spread the cost in interest-free biweekly installments of $130.

  • Deposit only

    Book now with just a 40% deposit. The remaining balance is due 95 days before departure.

  • $ - US Dollar

    You’ll encounter US Dollar in USA.

  • Plug types A, B

    You’ll need an adapter for these sockets in USA.

  • 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

      Used in USA

    • Type B

      Used in USA

  • Visa

    Whether you need a visa depends on your nationality and how long you stay. We can’t process visas for you, but here’s a quick indication for this trip.

    This is only an indication. Visa rules depend on your passport, trip length and purpose. Always confirm with the official embassy or consulate before you travel.

  • Payment information

    Pay now
    A 40% deposit
    Balance due
    95 days before departure
    Installments
    Interest-free, every two weeks
    Currency
    USD
    Booking fee
    None

    Book now with just a 40% deposit and pay the rest later. The remaining balance is due 95 days before departure, charged automatically to your card, or you can split it into interest-free biweekly installments of $130 at checkout. Everything is charged in USD, and TourRadar never adds a booking fee. Any trip departing before January 11th, 2027 will need to be paid in full at checkout.

    Accepted for Worldee tours

    • Visa
    • Maestro
    • Mastercard
    • American Express
    • PayPal

    TourRadar does NOT charge you an extra fee for using any of these payment methods.

  • Best price guarantee

    Found a lower price for the same tour elsewhere? We work directly with every tour operator, so we can match it.

    How it works

    1. Find a lower price

      Spot the same tour cheaper on another site or agency.

    2. Send us the quote

      Contact us before you book.

    3. We match it

      If the quote qualifies, you book with us at that price.

    Your quote needs

    • Same tour and operator
    • Same start and end dates
    • Same number of travelers
    • Same inclusions and destinations
    • Same booking and cancellation terms, in the same currency
    • A link to the site or agency offering it

    What doesn’t count

    • Quotes issued more than 24 hours ago
    • Cash back or loyalty program rebates
    • Itineraries that are similar but not identical
    • Similar tours run by a different operator
    • Bookings already confirmed on TourRadar

    Every new booking also counts toward your , which unlocks extra savings.

  • 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.

From
$757
15% off
US $643 per person
+ $3,481 additional upfront costs

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
Pay only 40% today. The rest is due 95 days before departure. Learn more

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.

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