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Illinois

Winding Through the Windy City: Art & Architecture in Chicago

Program No. 21908RJ

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Back Winding Through the Windy City: Art & Architecture in Chicago Winding Through the Windy City: Art & Architecture in Chicago

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2027

From Monday

May 3, 2027

To Saturday

May 8, 2027

From

2,399

Each

Select Date

1 Traveler

Shared Room

Winding Through the Windy City: Art & Architecture in Chicago

Program No. 21908

May

BEGINS

Chicago, IL

May

CONCLUDES

Chicago, IL

Duration

6 days

5 nights

What's Included

11 meals ( 5B, 3L, 3D )

2 expert-led lectures

9 expert-led field trips

An experienced Group Leader

Taxes and customary gratuity

Road Scholar Assurance Plan

Pay in Full 2,399

Pay Deposit 100

CUSTOMIZE YOUR TRIP

From Monday

May 3, 2027

To Saturday

May 8, 2027

From

2,899

Each

1 Traveler

Private Room (Just for You)

Winding Through the Windy City: Art & Architecture in Chicago

Program No. 21908

May

BEGINS

Chicago, IL

May

CONCLUDES

Chicago, IL

Duration

6 days

5 nights

What's Included

11 meals ( 5B, 3L, 3D )

2 expert-led lectures

9 expert-led field trips

An experienced Group Leader

Taxes and customary gratuity

Road Scholar Assurance Plan

Pay in Full 2,899

Pay Deposit 100

From Monday

May 3, 2027

To Saturday

May 8, 2027

From

2,399

Each

Select Date

2 Travelers

Winding Through the Windy City: Art & Architecture in Chicago

Program No. 21908

May

BEGINS

Chicago, IL

May

CONCLUDES

Chicago, IL

Duration

6 days

5 nights

What's Included

11 meals ( 5B, 3L, 3D )

2 expert-led lectures

9 expert-led field trips

An experienced Group Leader

Taxes and customary gratuity

Road Scholar Assurance Plan

Pay in Full 4,798

Pay Deposit 100

CUSTOMIZE YOUR TRIP

From Monday

May 17, 2027

To Saturday

May 22, 2027

From

2,499

Each

Select Date

Only 1 spot left

1 Traveler

Shared Room

Winding Through the Windy City: Art & Architecture in Chicago

Program No. 21908

May

BEGINS

Chicago, IL

May

CONCLUDES

Chicago, IL

Duration

6 days

5 nights

What's Included

11 meals ( 5B, 3L, 3D )

2 expert-led lectures

9 expert-led field trips

An experienced Group Leader

Taxes and customary gratuity

Road Scholar Assurance Plan

Pay in Full 2,499

Pay Deposit 100

CUSTOMIZE YOUR TRIP

From Monday

May 17, 2027

To Saturday

May 22, 2027

From

3,099

Each

1 Traveler

Private Room (Just for You)

Winding Through the Windy City: Art & Architecture in Chicago

Program No. 21908

May

BEGINS

Chicago, IL

May

CONCLUDES

Chicago, IL

Duration

6 days

5 nights

What's Included

11 meals ( 5B, 3L, 3D )

2 expert-led lectures

9 expert-led field trips

An experienced Group Leader

Taxes and customary gratuity

Road Scholar Assurance Plan

Pay in Full 3,099

Pay Deposit 100

From Monday

May 17, 2027

To Saturday

May 22, 2027

From

2,499

Each

2 Travelers

Winding Through the Windy City: Art & Architecture in Chicago

Program No. 21908

May

BEGINS

Chicago, IL

May

CONCLUDES

Chicago, IL

Duration

6 days

5 nights

What's Included

11 meals ( 5B, 3L, 3D )

2 expert-led lectures

9 expert-led field trips

An experienced Group Leader

Taxes and customary gratuity

Road Scholar Assurance Plan

Pay in Full 4,998

Pay Deposit 100

From Monday

Jun 21, 2027

To Saturday

Jun 26, 2027

From

2,449

Each

Select Date

1 Traveler

Shared Room

Winding Through the Windy City: Art & Architecture in Chicago

Program No. 21908

Jun

BEGINS

Chicago, IL

Jun

CONCLUDES

Chicago, IL

Duration

6 days

5 nights

What's Included

11 meals ( 5B, 3L, 3D )

2 expert-led lectures

9 expert-led field trips

An experienced Group Leader

Taxes and customary gratuity

Road Scholar Assurance Plan

Pay in Full 2,449

Pay Deposit 100

CUSTOMIZE YOUR TRIP

From Monday

Jun 21, 2027

To Saturday

Jun 26, 2027

From

2,999

Each

Select Date

1 Traveler

Private Room (Just for You)

Winding Through the Windy City: Art & Architecture in Chicago

Program No. 21908

Jun

BEGINS

Chicago, IL

Jun

CONCLUDES

Chicago, IL

Duration

6 days

5 nights

What's Included

11 meals ( 5B, 3L, 3D )

2 expert-led lectures

9 expert-led field trips

An experienced Group Leader

Taxes and customary gratuity

Road Scholar Assurance Plan

Pay in Full 2,999

Pay Deposit 100

CUSTOMIZE YOUR TRIP

From Monday

Jun 21, 2027

To Saturday

Jun 26, 2027

From

2,449

Each

Select Date

2 Travelers

Winding Through the Windy City: Art & Architecture in Chicago

Program No. 21908

Jun

BEGINS

Chicago, IL

Jun

CONCLUDES

Chicago, IL

Duration

6 days

5 nights

What's Included

11 meals ( 5B, 3L, 3D )

2 expert-led lectures

9 expert-led field trips

An experienced Group Leader

Taxes and customary gratuity

Road Scholar Assurance Plan

Pay in Full 4,898

Pay Deposit 100

CUSTOMIZE YOUR TRIP

From Monday

Jul 12, 2027

To Saturday

Jul 17, 2027

From

2,449

Each

Select Date

1 Traveler

Shared Room

Winding Through the Windy City: Art & Architecture in Chicago

Program No. 21908

Jul

BEGINS

Chicago, IL

Jul

CONCLUDES

Chicago, IL

Duration

6 days

5 nights

What's Included

11 meals ( 5B, 3L, 3D )

2 expert-led lectures

9 expert-led field trips

An experienced Group Leader

Taxes and customary gratuity

Road Scholar Assurance Plan

Pay in Full 2,449

Pay Deposit 100

CUSTOMIZE YOUR TRIP

From Monday

Jul 12, 2027

To Saturday

Jul 17, 2027

From

2,999

Each

Select Date

1 Traveler

Private Room (Just for You)

Winding Through the Windy City: Art & Architecture in Chicago

Program No. 21908

Jul

BEGINS

Chicago, IL

Jul

CONCLUDES

Chicago, IL

Duration

6 days

5 nights

What's Included

11 meals ( 5B, 3L, 3D )

2 expert-led lectures

9 expert-led field trips

An experienced Group Leader

Taxes and customary gratuity

Road Scholar Assurance Plan

Pay in Full 2,999

Pay Deposit 100

CUSTOMIZE YOUR TRIP

From Monday

Jul 12, 2027

To Saturday

Jul 17, 2027

From

2,449

Each

Select Date

2 Travelers

Winding Through the Windy City: Art & Architecture in Chicago

Program No. 21908

Jul

BEGINS

Chicago, IL

Jul

CONCLUDES

Chicago, IL

Duration

6 days

5 nights

What's Included

11 meals ( 5B, 3L, 3D )

2 expert-led lectures

9 expert-led field trips

An experienced Group Leader

Taxes and customary gratuity

Road Scholar Assurance Plan

Pay in Full 4,898

Pay Deposit 100

CUSTOMIZE YOUR TRIP

From Monday

Sep 6, 2027

To Saturday

Sep 11, 2027

From

2,449

Each

Select Date

1 Traveler

Shared Room

Winding Through the Windy City: Art & Architecture in Chicago

Program No. 21908

Sep

BEGINS

Chicago, IL

Sep

CONCLUDES

Chicago, IL

Duration

6 days

5 nights

What's Included

11 meals ( 5B, 3L, 3D )

2 expert-led lectures

9 expert-led field trips

An experienced Group Leader

Taxes and customary gratuity

Road Scholar Assurance Plan

Pay in Full 2,449

Pay Deposit 100

CUSTOMIZE YOUR TRIP

From Monday

Sep 6, 2027

To Saturday

Sep 11, 2027

From

2,999

Each

Select Date

1 Traveler

Private Room (Just for You)

Winding Through the Windy City: Art & Architecture in Chicago

Program No. 21908

Sep

BEGINS

Chicago, IL

Sep

CONCLUDES

Chicago, IL

Duration

6 days

5 nights

What's Included

11 meals ( 5B, 3L, 3D )

2 expert-led lectures

9 expert-led field trips

An experienced Group Leader

Taxes and customary gratuity

Road Scholar Assurance Plan

Pay in Full 2,999

Pay Deposit 100

CUSTOMIZE YOUR TRIP

From Monday

Sep 6, 2027

To Saturday

Sep 11, 2027

From

2,449

Each

Select Date

2 Travelers

Winding Through the Windy City: Art & Architecture in Chicago

Program No. 21908

Sep

BEGINS

Chicago, IL

Sep

CONCLUDES

Chicago, IL

Duration

6 days

5 nights

What's Included

11 meals ( 5B, 3L, 3D )

2 expert-led lectures

9 expert-led field trips

An experienced Group Leader

Taxes and customary gratuity

Road Scholar Assurance Plan

Pay in Full 4,898

Pay Deposit 100

CUSTOMIZE YOUR TRIP

From Monday

Sep 20, 2027

To Saturday

Sep 25, 2027

From

2,449

Each

Select Date

1 Traveler

Shared Room

Winding Through the Windy City: Art & Architecture in Chicago

Program No. 21908

Sep

BEGINS

Chicago, IL

Sep

CONCLUDES

Chicago, IL

Duration

6 days

5 nights

What's Included

11 meals ( 5B, 3L, 3D )

2 expert-led lectures

9 expert-led field trips

An experienced Group Leader

Taxes and customary gratuity

Road Scholar Assurance Plan

Pay in Full 2,449

Pay Deposit 100

CUSTOMIZE YOUR TRIP

From Monday

Sep 20, 2027

To Saturday

Sep 25, 2027

From

2,999

Each

1 Traveler

Private Room (Just for You)

Winding Through the Windy City: Art & Architecture in Chicago

Program No. 21908

Sep

BEGINS

Chicago, IL

Sep

CONCLUDES

Chicago, IL

Duration

6 days

5 nights

What's Included

11 meals ( 5B, 3L, 3D )

2 expert-led lectures

9 expert-led field trips

An experienced Group Leader

Taxes and customary gratuity

Road Scholar Assurance Plan

Pay in Full 2,999

Pay Deposit 100

From Monday

Sep 20, 2027

To Saturday

Sep 25, 2027

From

2,449

Each

Select Date

2 Travelers

Winding Through the Windy City: Art & Architecture in Chicago

Program No. 21908

Sep

BEGINS

Chicago, IL

Sep

CONCLUDES

Chicago, IL

Duration

6 days

5 nights

What's Included

11 meals ( 5B, 3L, 3D )

2 expert-led lectures

9 expert-led field trips

An experienced Group Leader

Taxes and customary gratuity

Road Scholar Assurance Plan

Pay in Full 4,898

Pay Deposit 100

CUSTOMIZE YOUR TRIP

From Monday

Oct 18, 2027

To Saturday

Oct 23, 2027

From

2,399

Each

Select Date

1 Traveler

Shared Room

Winding Through the Windy City: Art & Architecture in Chicago

Program No. 21908

Oct

BEGINS

Chicago, IL

Oct

CONCLUDES

Chicago, IL

Duration

6 days

5 nights

What's Included

11 meals ( 5B, 3L, 3D )

2 expert-led lectures

9 expert-led field trips

An experienced Group Leader

Taxes and customary gratuity

Road Scholar Assurance Plan

Pay in Full 2,399

Pay Deposit 100

CUSTOMIZE YOUR TRIP

From Monday

Oct 18, 2027

To Saturday

Oct 23, 2027

From

2,899

Each

1 Traveler

Private Room (Just for You)

Winding Through the Windy City: Art & Architecture in Chicago

Program No. 21908

Oct

BEGINS

Chicago, IL

Oct

CONCLUDES

Chicago, IL

Duration

6 days

5 nights

What's Included

11 meals ( 5B, 3L, 3D )

2 expert-led lectures

9 expert-led field trips

An experienced Group Leader

Taxes and customary gratuity

Road Scholar Assurance Plan

Pay in Full 2,899

Pay Deposit 100

From Monday

Oct 18, 2027

To Saturday

Oct 23, 2027

From

2,399

Each

Select Date

2 Travelers

Winding Through the Windy City: Art & Architecture in Chicago

Program No. 21908

Oct

BEGINS

Chicago, IL

Oct

CONCLUDES

Chicago, IL

Duration

6 days

5 nights

What's Included

11 meals ( 5B, 3L, 3D )

2 expert-led lectures

9 expert-led field trips

An experienced Group Leader

Taxes and customary gratuity

Road Scholar Assurance Plan

Pay in Full 4,798

Pay Deposit 100

CUSTOMIZE YOUR TRIP

You’ve hit a bump in the road.

We apologize, but we’re having some technical problems right now. You can either try again later or give us a call at (800) 454-5768, Monday-Friday, 9am – 6:30pm ET.

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May 3 - May 8, 2027

May 17 - May 22, 2027

Jun 21 - Jun 26, 2027

Jul 12 - Jul 17, 2027

Sep 6 - Sep 11, 2027

Sep 20 - Sep 25, 2027

Oct 18 - Oct 23, 2027

Looking to travel in 2027?

We are limiting the advanced purchase of airfare for travel in 2027. If you see the option to select Gateway Airport when you are enrolling, please do so. Otherwise, select Custom Flight Arrangements and your preferred airport. We will send you your preliminary flight itinerary for your review about seven months before your departure.

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Travel Information, Transportation Details & Required Documents

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May 3 - May 8, 2027

May 17 - May 22, 2027

Jun 21 - Jun 26, 2027

Jul 12 - Jul 17, 2027

Sep 6 - Sep 11, 2027

Sep 20 - Sep 25, 2027

Oct 18 - Oct 23, 2027

Documents

Personal Information and Preferences

After you enroll, we’ll ask you to provide or update your personal information and preferences, which includes your health information, lodging and meal preferences for your program.

Visas

United States citizens don’t need a visa for any of the countries you’ll be visiting. Non-U.S. citizens should refer to their country's requirements to ensure they have the necessary documentation for travel.

Traveling by Air

Plane

Arrival day is on Monday, May 3, 2027.

Meet the group at Hyatt Place Chicago River North in Chicago, IL

Start of Trip: 3:00-5:00 p.m. hotel check-in and Program Registration; 6:30 p.m. Welcome Dinner followed by Orientation.

Your trip ends on: Saturday, May 8, 2027 in Chicago, IL at Hyatt Place Chicago River North

End of Trip: 9:00 a.m. after breakfast; 12:00 Noon hotel check-out.

Ground Transportation Options

Program Arrival Airport

Chicago Midway

CTA

Train

Take the Orange line to the Clark/Lake station. From there is it about 1/2 mile walk to the hotel.

Program Arrival Airport

Chicago O'Hare

CTA

Train

*Advanced reservations are not required.

Take the blue line to the Clark/Lake station. From there, it is about a 1/2 mile to the hotel.

Program Arrival Airport

O'Hare International Airport (ORD)

The estimated travel time to the check-in location is 45 minutes approximately .

The estimated distance to the check-in location is 17 miles .

Taxi

Cost: Please call transfer service directly for rates. Prices subject to change.

*Advanced reservations are not required.

Available curb side at the airport. Prices are subject to change.

Program Arrival Airport

Chicago Midway International Airport (MDW)

The estimated travel time to the check-in location is 40 minutes .

The estimated distance to the check-in location is 15 Miles .

CTA

Public Transportation

Cost: Please call transfer service directly for rates. Prices subject to change.

*Advanced reservations are not required.

Take the Orange & Red Lines to the Grand stop. Hotel is 5 minute walk away.

Program Arrival Airport

Chicago Midway International Airport (MDW)

The estimated travel time to the check-in location is 30-40 minutes .

The estimated distance to the check-in location is 15 miles .

Taxi

Cost: Please call transfer service directly for rates. Prices subject to change.

*Advanced reservations are not required.

Available curb side at the airport. Prices are subject to change.

Traveling by Car

Car

Arrival day is on 5/3/2027.

Meet the group at Hyatt Place Chicago River North in Chicago, IL.

Start of Trip: 3:00-5:00 p.m. hotel check-in and Program Registration; 6:30 p.m. Welcome Dinner followed by Orientation.

Your trip ends on: Saturday, May 8, 2027 in Chicago, IL at Hyatt Place Chicago River North.

End of Trip: 9:00 a.m. after breakfast; 12:00 Noon hotel check-out..

Parking

Valet and self parking are both available with unlimited in-and-out privileges. Please contact the hotel for current rates.

Directions

Directions to Hyatt Place Chicago River North

From the Madison, Wisconsin Area: Take I-90E/I-39S Janesville to I-90/I-94 east to Chicago. Take exit 50B (Ohio Street East). Travel 1 mile to La Salle Street. Take a right turn at La Salle Street to Illinois Street. Left on Illinois Street to 66 W Illinois Street. Hotel will be on the left side of the street. From Indianapolis area: Take I-65 North to Exit 262 where you will take the ramp for I-90 West towards Chicago. Follow I-90W to I-94W Dan Ryan Expressway. Exit at Ohio East (Exit 50B) Travel 1 mile to La Salle Street. Take a right turn at La Salle Street to Illinois Street. Left on Illinois Street to 66 W Illinois Street. Hotel will be on the left side of the street.

You’ve hit a bump in the road.

We apologize, but we’re having some technical problems right now. You can either try again later or give us a call at (800) 454-5768, Monday-Friday, 9am – 6:30pm ET.

Help & Support

(800) 454-5768

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Help & Support

(800) 454-5768

Get in Touch

Web Help

App Help

Apply for Financial Aid

About Us

About Road Scholar

Why Go With Us

Careers

Press

Giving

Trip Planning

Find a Trip

See the Map

Before You Go

Request a Catalog

Organize a Group Trip

Trip Terms and Conditions

Community

Blog

Lifelong Learning Institutes

Become an Ambassador

Alumni Groups

More to Explore

Bookshop

Campus Store

Partnerships

PO Box 56033 Boston, MA 02205-6033

Road Scholar educational adventures are created by Elderhostel, the not-for-profit world leader in educational travel since 1975. The Federal Tax Identification number (EIN) for Elderhostel, Inc DBA Road Scholar is 04-2632526

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