Chicago
The Best of the Windy City
May 17 - May 22, 2027
Chicago
May 17 - May 22, 2027Highlights
- Stay along the Magnificent Mile
- Learn about Architecture aboard a River Cruise
- Taste Chicago's iconic foods
- Tour Oak Park, designed by Frank Lloyd Wright
- Visit Wrigley Field
- Time to explore personal interests
- Suggestions for things to see and do
- And More... See itinerary for details
Itinerary
Monday, 17 May 2027: Arrive Chicago; Welcome Meeting & Dinner (D)
Schedule your arrival into either Chicago O'Hare (ORD) or Chicago Midway (MDW) airport, depending on which provides the best flight options for you. Plan to arrive no later than 4:00pm and take local transportation to our hotel. The tour begins promptly at 6:00pm in the lobby of our hotel. We will make introductions and then enjoy dinner together to get better acquainted. Overnight Chicago - 5 nights
Tuesday, 18 May 2027: Millennium Park & Walking Tour of "The Loop;" Willis Tower (B,L)
We begin today with an engaging walk through Chicago's North Loop, an area defined by the elevated train lines that form a circuit in the heart of the city. We'll learn how the Great Fire of 1871 started and marvel at the modern city that rose from the ashes of the old. We'll also see the iconic Chicago Theatre marquee, the Tiffany mosaic hidden in plain sight, and the start of the legendary Route 66. This afternoon, we're off to Willis Tower where we'll take in a different view of Chicago as we ride up 103 floors to the Skydeck for a view spanning four states! Test your adrenaline, if you dare, by stepping out onto The Ledge to see the city below.
Wednesday, 19 May 2027: Pizza Tour & Tasting; Architectural Boat Cruise (B,L)
This is a leisurely morning to spend as you wish getting further acquainted with the area around our hotel. Mid-morning we depart for a tour that can only be found here -- a Chicago Pizza Tour! We'll learn more about the history of pizza making and what makes Chicago-style so special as we visit neighborhood pizzerias and talk with the proprietors. This afternoon we enjoy views from yet another angle... the water. Cruise the Chicago River on this guided adventure highlighting Chicago's most famous architectural sites. This evening is yours. Perhaps you'll want to continue exploring the Riverwalk area or take in one of the city's famed comedy shows.
Thursday, 20 May 2027: Frank Lloyd Wright's Oak Park; Free Afternoon (B)
This morning we're off to Oak Park to visit the home and studio of Frank Lloyd Wright, which has been restored to its 1909 prairie-style appearance. We learn how his career in architecture was shaped by his time in Chicago. After touring his home there will be time to wander around Oak Park where you can view as many as 25 other works of art by Wright. This afternoon is yours to enjoy as you wish. Your Tour Leader will have plenty of suggestions, but some suggestions you might consider ate the Art Institute of Chicago to view the immense pointillist painting by Georges Seurat, or visit the renowned Field Museum of Natural History, one of the largest in the world.
Friday, 21 May 2027: Visit Wrigley Field; Free Afternoon; Farewell Dinner (B,D)
Today we visit Wrigley Field, home of the Chicago Cubs! Another must do in Chicago even you aren't a baseball fan. We'll visit the second oldest Major League Baseball park and see the manual scoreboard still used today. This afternoon is yours to enjoy as you wish, to see some more of the impressive sights of Chicago or its world class museums. We regroup this evening for our Farewell Dinner and recount our adventures of the week.
Saturday, 22 May 2027: Depart for Home (B)
Sadly, our time together has come to an end. Make your return flight at your convenience. Based on the departure time you provide WTT, your Tour Leader can assist with organizing travelers into small groups so you can ride-share to the airport if you wish.
Chicago
May 17 - May 22, 2027Pricing
Room Share
$2,552.00Single Room
$3,579.00Non-Members
ADD $50.00Status of this Tour
Space Available
Tour Pricing Includes
- All meals and activities expressly listed in the itinerary, PLUS...
- All tipping of local guides and coach drivers
- WTT Tour Leader to enhance the individual & group experience
- Arranged room sharing with another solo traveler
- Travel Dollar credits (a benefit of WTT membership) toward future travel with WTT
Not Included In The Price
- Airfare or other transportation to and from the tour
- Meals and activities not specified in the itinerary
- Beverages other than coffee, tea & still water unless otherwise noted
- Arrival or Departure Transfers
- Any personal expenses or expenditures
- Any pre- or post- tour arrangements
- Any gratuities for the WTT Tour Leader
- Trip Cancellation / Trip Interruption Insurance
Payment Dates -and- Cancellation Terms for This Tour
You have 3 days to cancel and receive a refund. Thereafter, the amount required at time of reservation is non-refundable and the following cancellation penalties will be enforced.
Wednesday, 18 Nov 2026: Last day $250 deposit can be converted to a credit for use on a new reservation; thereafter the deposit is forfeited.
Tuesday, 16 Feb 2027: Balance Due. Cancellation after this date but before Friday, 2 Apr 2027 results in a cancellation penalty of 50% of your Total Tour Cost.
Friday, 2 Apr 2027: Cancellation on or after this date results in a cancellation penalty of 100% of your Total Tour Cost.
Using Parked Credits: If traveler cancels during the 3-day cancel without penalty period, used credits will be re-parked with the original expiration date(s). Thereafter, cancellation will result in forfeiture of the total amount of parked credits used. If applicable, additional cancellation penalties will be assessed based on date of cancellation.
To Cancel: Should you need to cancel after your space on this tour is confirmed, you must use the Cancellation Form. Cancellation penalties are based on the date we receive your cancellation form. No other method of communicating a cancellation will be accepted.
Insurance Reminder
Chicago
May 17 - May 22, 2027Flights, Transfers & Lodging
Arrival & Departure Information
Travelers will make their own air arrangements as follows:
When searching for flights for this trip, be sure to search "Multi-city" or "Multiple Destinations." For comparison, you may also want to search for one-way fares.
Arrival Airport: CHI - Chicago, US (Greater Chicago Airports (ORD, MDW))
Arrival Date: Monday, May 17. Arrive by 4:00pm.
Arrival Transfer: Use local shuttle or taxi. Details provided in Final Travel Instructions.
Departure Airport: CHI - Chicago, US (Greater Chicago Airports (ORD, MDW))
Departure Date: Saturday, May 22nd. Depart at your convenience.
Departure Transfer: Use local shuttle or taxi service. WTT Tour Leader will assist in coordinating ride sharing.
When to Book Your Air
It is up to you to decide how soon you want to make your travel arrangements, however we recommend waiting until you receive your final payment invoice. You will still have plenty of time to get your air (about 4 months).
Once you have booked your flights (or other transportation arrangements), use the Travel Arrangements Form to send WTT your flight details. Use the same form to update your information should it change.
Airport Transfer Information
Getting from the airport to the hotel (i.e. the arrival transfer) can be a point of concern for some travelers. Locate the "Arrival and Departure Information" -OR- "Want to Arrive a Day Early?" on this page for arrival transfer information.
When arrival transfers are not included: WTT will provide suggestions to get to the hotel in your Final Travel Instructions about 2-3 weeks before the start of the tour. You'll also be able to see who else is arriving at the same time if you want to coordinate ride-sharing to the hotel.
Don't Worry. We're Expecting You: One of the reasons we ask for your travel arrangements is so we know when you're arriving and can approximate when you should be at the hotel. Your Final Travel Instructions will have instructions on what to do and who to contact if your flight is delayed.
Lodging / Hotels
Chicago: Embassy Suites Chicago Downtown Magnificent Mile
Whenever possible, we choose hotels that are near the city center and/or where there are things to do and places to eat within walking distance of the hotel. When the chosen hotel is not within walking distance of much, transportation options, at the traveler's expense, are typically available.
In the unlikely event WTT is unable to provide the hotel accommodation(s) listed, for whatever reason, WTT will substitute similar quality accommodation(s) at no additional cost to the traveler.
Want to Arrive a Day Early?
Worried about possible flight delays? Consider arriving one day before the official tour start date. Many of our travelers choose this optional service. Your pre-tour package includes:
- The room (standard check-in times apply)
- Breakfast the following morning
- Optional activity suggestions prior to tour
$206.00 Roomshare pp $411.00 Single Occupancy
The pre-tour package is an optional service. Rates are established at time of tour posting. Early check-in is solely at the discretion of the hotel and cannot be arranged in advance.
Early Arrival Hotel: This tour uses the same hotel used on the first night of the tour.
Chicago
May 17 - May 22, 2027Destination Information
What do others say about this tour and traveling with WTT?
How Does Room Sharing Work?
On the Reservation Form there are 3 choices regarding room-sharing.
Note: Certain room-types may be unavailable at the time you make your reservation. If a room-type is unavailable the choice will be greyed out.
- Select "Yes, I want to share a room" and WTT will assign you a roommate when Final Travel Instructions are sent.
- You can specify a roommate by entering her name where indicated. If your named roommate is not on the tour, for any reason, WTT will assign you a roommate unless you pay to have your own room, if available.
- Select "No, I do not wish to share a room" if you want to have your own room. Additional costs apply.
- All shared rooms have 2 beds
- All shared rooms are non-smoking
- No special requests about your roommate can be accommodated
- See "Frequently Asked Questions" TAB for more details
How Active is this Tour?
- 50% Easy
- 50% Moderate (extensive urban walking; use of public transportation; stairs)
Your Responsibilities as a Solo Traveler
As a solo traveler you are responsible for yourself, your possessions, your physical fitness, and all other aspects related to participation in the WTT tour you have chosen. Be sure to read the itinerary closely to better understand the physical requirements necessary for the tour.
WTT tours are not suitable for anyone whose mobility is challenged or compromised. If you struggle with walking, standing or negotiating stairs or if you are in doubt as to your ability to meet the physical activity requirements, you should not sign up for this trip.
What is the Group Size?
You will be introduced to the WTT Tour Leader when you receive your Final Travel Instructions, about 2-3 weeks before the tour begins.
Learn about your fellow travelers after final payment by visiting MyWTT. Room sharing assignments will be listed in the Final Travel Instructions.
What meals are included and how are dietary restrictions accommodated?
Each day of the itinerary lists the included meals for that day (B,L,D,O=Other). When a meal is not included, the WTT Tour Leader will have suggestions for where to eat.
You do not have to dine alone unless it is your personal choice. You'll most likely be dining with new acquaintances you've made, or you can join the Tour Leader.
Dietary Restrictions: Vegetarian and gluten-free dietary restrictions can be accommodated on this tour with limited selections.
What clothing and items should I pack for this trip?
In general the temperature, rainfall and humidity levels vary based on the time of the year. We suggest you monitor weather apps leading up to the time you depart for the most current information.
For This Trip You May Want—
- Comfortable walking shoes
- Smart-casual wear if you'd like to dress up a bit for dinners
- Jacket/sweater for brisk days
- Inexpensive rain poncho or travel umbrella, just in case
Good Packing Habits—
- Bring what you need to get a good night's sleep, such as ear plugs, white noise generator, sleeping aids, etc. Unfamiliar noises of all types can disrupt your rest.
- Pack a limited amount of comfortable, casual clothing that layer and coordinate. Your fellow travelers will not mind or even notice – seeing you in the same clothing.
- Bring only two pairs of everyday shoes: one pair of well-broken-in walking shoes, and a second pair that could do double-duty as a walking shoe or a slightly dressy shoe.
- Pare down your beauty regimen to the bare minimum and always pack travel-sized toiletries.
- Pack medication in your carry-on and pack only as much as needed for the duration of your tour plus a few extra days as a precaution.
What are the luggage restrictions for this tour?
- We strongly recommend you bring only one suitcase plus small shoulder bag/day pack/purse.
- You are responsible for managing your own belongings.
How much money should I bring on this tour?
What are the tipping guidelines for this tour?
- You are responsible for tipping waitstaff, porters, or other individuals who provide a service to you at the hotel, or other public locations.
- You may want to tip your WTT Tour Leader for an outstanding job. The amount is entirely a personal preference. If you'd like a guideline, consider $8-$10 per day.
Can I transfer my deposit to another tour?
To get off this tour and register for another tour, you must follow these steps - in the order shown:
2) WAIT before submitting your new reservation! You must receive the Cancellation Confirmation email before submitting your new reservation. This can take up to 2 business days. The Cancellation Confirmation email will list the amount of parked credits from this tour that are now available to use on a new reservation.
3) COMPLETE the new Reservation Form and USE the parked credits towards your deposit on the new tour.
Note: If you used Parked Credits to pay the deposit on this tour, these credits cannot be used a second time and are not eligible to be transferred.
What happens if I need to cancel this tour?
Chicago
May 17 - May 22, 2027SPACE RESERVATION REQUEST
If becoming a member and signing up for a tour at the same time, you only need to fill out this form.
Our Promise to You
It doesn’t matter which tour you choose.
You’ll find your people and make memories that last a lifetime.