Congratulations on making a reservation with Singles Travel International for your next vacation!

WHAT NEXT? Complete your profile and post a message on the chat to say hello to your fellow travelers.

REVIEW the important information on the FAQ tab for this trip and visit our Help Center. We strongly encourage all our members to check the latest travel recommendations by the (for international trips only, and please tie to country-specific pages on each of these sites and then add the correct link  US State Department, CDC and air carriers to review the latest information for travel risks in order to make an informed decision about their travel safety.

SOCIALIZE Say hello to your fellow travelers on the chat and start enjoying our live, virtual community events for Singles 50+ where you meet singles your age all year round. Sign Up Today!

DON’T MISS OUT Get the best deals on optional “Add-ons.” Review the Trip Options and make all reservations so you don’t miss out on any limited or time-sensitive offers.

INSURANCE Travel Insurance is not mandatory, but, based on our experience, we highly recommend it. In addition to direct access immediately upon completing your purchase, you will receive a quote from Travel Guard regarding travel insurance after reserving your vacation.

When selecting a travel insurance policy, we recommend that at a minimum you are covered for medical expenses including emergency evacuation and repatriation. We also strongly recommend that the policy cover personal liability, cancellation, curtailment and loss of luggage and personal effects.

If you have any questions, Travel Guard professional, expert agents are available 24 hours a day, 7 days a week. Call us, if you have not received your quote within 3 days, or CLICK HERE to go directly to Travel Guard and request a policy quote. It only takes a few minutes.

Questions and comments after you have reserved your vacation are addressed promptly when you send a message to us at service@singlestravelintl.com.

FINAL PREPARATION Your “Final Vacation Details & Meetup Information” including transportation and how to meet up with the group will be available on the YOUR TRAVEL DOCUMENTS button on the left navigation bar on the trip site, 21 days prior to trip start date.

Questions and comments after you have reserved your vacation are addressed promptly when you send a message to us at service@singlestravelintl.com.

The tour begins in Chicago at 3:00 p.m. on Friday, August 29, 2025 and ends in Chicago on Monday morning, September 1, 2025. Therefore the trip is 3 nights/4 days.

Add an extra day at the beginning for more fun, entertainment and socializing.  Select our “Extra Fun Hotel Package in Chicago – Your Own Space™” on the Book Now page when you check out. 

All cancellations must be made in writing to Singles Travel International at service@singlestravelintl.com and are subject to per person penalties as follows:

After deposit and at any time of cancellation, refunds may be requested less a minimum charge of $150 in addition to other penalties listed below.

*After May 28, 2025 – 100% penalty applies

Air packages and air tickets are subject to cancellation policies imposed by the airlines.

Cancellations made prior to the final payment date of May 28, 2025, may request a Future Trip Credit for the Singles Travel International portion of $150 and our minimum cancellation fee will be waived, but not refunded. The Future Trip Credit may be used toward any future Singles Travel International vacation within 1 year of cancellation, for travel at any time. No refunds will be given on any unused portions of the trip.

To make the most of your weekend, we recommend that you arrive at the Hampton Inn Chicago Downtown/North Loop by 3:00 p.m. on Friday, August 29, 2025. Note that check-in is at 3:00 p.m. in order to connect with our Concierge at the Singles Travel International Hospitality Desk,  check-in and join the group for this evening’s festivities!  In the event that you arrive early, the bell desk will gladly hold your bags while you’re out on the town.

Hampton Inn Chicago Downtown/North Loop
68 E Wacker Pl., Chicago, IL 60601
Phone: 312-419-9014

Singles Travel International is a vacation event company that plans singles events and markets our events at our expense to create a “singles only” experience. We do not allow guests to join the group unless the reservation has been made by Singles Travel International. Our policy is firm for tours and cruises, as well as pre and post trip hotel stays. Members and friends that “show up” will not be allowed to participate.

Yes! Singles Travel International is the only singles vacation company that features a travel community where members may send messages to one another at any time. Once you make a reservation, you are invited to post messages on the trip chat, which is great for finding out more about your fellow travel companions, coordinating taxi shares, setting up tours and more. Your trip chat is accessible from the trip page. Ask your Singles Travel International Reservation Guide for assistance.

Our program for 50+ singles also includes live online events and virtual tours plus a virtual Meet & Greet with your travel companions before you depart. View and get reminders for each event on our community page, www.SingleLife.Today.  Be sure to sign up today so that you don’t miss out on anything!

In order to accommodate singles from all over the world, our tours and cruises are priced as land only. Therefore, airfare is additional. Singles Travel International is a licensed ticketing agency and oftentimes has low negotiated fares.

To make the most of your weekend, we recommend that you arrive by 3 p.m. on Friday, August 29, 2025, and depart any time after breakfast on Monday, September 1, 2025. Note that Chicago is served by 2 airports, Midway  (MDW) and O’Hare (ORD). Both are approximately the same distance to downtown, so book the airport with the best airfare.

DRIVING?
Are you already in the area?  Self Parking is available at the hotel for $50 per day.

The least expensive transportation in Chicago is available via rail for approximately $2.25 each way. Visit Chicago Transit Authority for rail/bus info. From O’Hare, take the Blue Line (Forest Park) to Washington Station and walk 7 minutes to the hotel or grab a taxi. From Midway Airport, take the Orange Line (Loop) to State/Lake and walk 4 minutes to the hotel.

Alternate service is available via taxi outside each terminal at O’Hare and Midway.

For a taxi ride from O’Hare Airport (ORD) to 68 E. Wacker Pl, Chicago, IL 60601, expect to pay approximately $65 to $80. This fare typically includes tolls and reasonable luggage for up to two passengers.

For a taxi ride from Midway Airport (MDW) to the same destination, the cost is generally around $40 to $60. Again, this price includes tolls and luggage for two passengers

Our tour does not include airfare, airport transfers, 2 lunches and 1 dinner. You are responsible for alcoholic beverages (except when included in our events), incidentals such as laundry and phone calls, plus gratuities to Singles Travel International Concierge ($15 per day) and local guides.  Our weekend in Chicago is a walking weekend. In other words, all of our activities are within walking distance (6-8 blocks or closer). If you require transportation, we will gladly assist and fares are at your own expense.

Our affordable Premium Memberships allows solo travelers the ability to have Your Own Space™️️ for a lot less so that you never have to share. Review the special Premium Member rates on the Book Now page. You may join at the same time that you purchase your vacation or click here to learn more and purchase your membership.

Roommate matches are available by request if you already have a traveling companion. Contact us at 877-SOLO-TRIP to speak with one our teammates to make your reservation.

Please contact your preferred carrier directly to make your reservation. If Singles Travel International issues a promotional economy fare, granting of frequent flyer credit is entirely at the airline’s discretion. If the flights are eligible, to ensure you earn frequent flyer credit from the airline, give your frequent flyer account number when you check in for your flights. In addition, save your boarding passes and the passenger receipt from your airline ticket. You may need to submit these to the airline (not to Singles Travel International) to claim any credit allowed.

The Hampton Inn Chicago Downtown/North Loop/Michigan Avenue, our home for the weekend is a comfortable and perfectly located hotel for maximizing our time in Chicago.  Although not a luxury property, it has all the amenities that we’ll need for a weekend getaway.

Plus, your Singles Travel International Concierge Team will be on hand to take care of your every need. It’s not only what we do, it’s who we are!

Of course not. You will be pleased to find out that nearly 90% of our guests on every trip sign up and have never met anyone before joining the group. In 31 years, we have perfected the singles vacation experience. It is paramount that our guests meet each other right away and have opportunities to mingle every day. From the moment you join our tour, our heroes, the Singles Travel International Concierge team is waiting to meet you. Our first day begins with a get together and the camaraderie builds as we go along.

As a travel club, matchmaking is not our focus. We offer an opportunity for single travelers to see the world in the company of other singles and do not guarantee ratios or ages. Our vacations are specifically designed for Baby Boomers and active travelers with an average age range of 50-70. We generally have a ratio of 60/40, women to men. Ages listed on our page are not restricted. They are simply used as a guideline.

We recommend that you meet the members of the Singles Travel International Community online where you may view and interact with members via “Who’s Going” on every trip page. This is the best way to find out exactly who will be on your vacation.

We encourage our members to complete their personal profiles including a photo. Knowing who’s on the trip in advance makes socializing before and during your vacation easier and more fun.

Chicago summers are are like none other, especially cooler by the lake as we near September. What a pleasant time to visit! Expect daytime high temperatures to be in the low 80s. Evening temperatures are generally in the mid 70s. Rain is always possible, so come prepared with rain gear.

There is no baggage limit at the hotel.

Currently, most airlines will allow you to check two bags, weighing 50 pounds each, for a fee. In addition you may carry-on one bag plus a personal item such as a purse or briefcase. Please check with your air carrier for up-to-the minute regulations and fees for checked baggage.

Since temperatures are warm, summer clothing is best. Remember to bring comfortable shoes and a jacket for evenings. Casual attire is acceptable throughout the weekend. However, you may want to bring something dressy for Sunday night at Morton’s. Jackets for gentleman are not required.

Packing Tips: Take only what you need; don’t over pack. Save room for souvenirs and purchases. Pack flat and full to avoid wrinkling. Bring wardrobe basics; mix and match around one or two colors. Don’t pack anything valuable, fragile or perishable. Label your luggage with an outside tag, and place an identification card inside each suitcase.

Essential Items: We highly recommend that you bring the following items.

– A great attitude and an open mind.
– A good, comfortable pair of broken-in walking shoes. You’ll log 10,000+ steps a day!
– A pair of shoes for restaurants (loafers, sandals, etc).
– Collapsible umbrella (which can double as a sunshade parasol) and/or lightweight raingear.
– Ladies may wish to bring an evening wrap and gentlemen a nicer jacket for evening wear.
– Sunglasses, sun block, sun hat or visor.
– Binoculars for Jazz Fest
– Toiletries: all your daily essentials.
– Prescription medications: sufficient supply for the entire trip plus legible written prescription in case of loss. Keep medications in their original, labeled container. Always pack your medications in your carry-on bag!
– Eyeglasses, contacts, contact lens solution. You may want to bring along a written prescription for your eyewear in case of loss.
– Over the counter medications: cold remedy, aspirin/pain reliever, antacid/stomach upset remedy, Band-Aids, anti-bacterial medication.
– Travel alarm clock with illuminated face.
– Small, Swiss Army type utility knife, great for opening wine, packages etc. Remember to pack this in your checked luggage!
– Travel journal/notepad and reading material.
– Home address book for sending postcards. A useful tip to avoid bringing your entire address book is to pre-write names and addresses of people to whom you want to send postcards on sheets of self-adhesive labels. It saves time and space in your luggage.
– Small, basic sewing kit with a few extra buttons. Remember to pack scissors in your checked bag!
– Photography Equipment: Bring a sufficient supply of film and extra batteries.

Questions and comments after you have reserved your vacation are addressed promptly when you send a message to us at service@singlestravelintl.com.

Your “Final Vacation Details & Meetup Information” including transportation and how to meet up with the group will be available on the YOUR TRAVEL DOCUMENTS button on the left navigation bar on the trip site, 21 days prior to trip start date.  We suggest you leave a copy of this with your family.

Internet access is available almost everywhere, including our hotel.

Our office is open Monday-Friday from 9:00 a.m. to 5:00 p.m. Eastern Standard Time. In an emergency after hours, please contact Tammy Weiler via What’s App at 815-715-6998.