Who is Windy City Travel

Let us share our knowledge with you to make your next vacation, destination wedding, honeymoon or event, your most memorable.

Windy City Travel has been in business as a full-service travel agency in the Old Town neighborhood of Chicago since 1981. The staff is renowned for providing personalized service for all your leisure and corporate travel needs including vacations, group travel, honeymoons, cruises and destination weddings. Our advisors have traveled the globe and are able to provide information and suggestions to truly tailor a trip to meet your needs and preferences.

In our aim to provide the best service, we offer you unbiased information on your best air, car, hotel, rail, tour and cruise options. Our preferred relationships will be available to you with value-added amenities and supplier discounts.

Problem Solving
Supplier Relationships

Where would you like to go?



Australia & New Zealand



North/Central/South America

What type of trip are you planning?

vacation planning

Land Vacations

Escorted Tours & Safaris, Beach Vacations, All Inclusives

cruise planning


River and Oceanic. Europe, Alaska, Caribbean

group travel and vacation planning


Family & Friends, Business Meetings & Conferences, Destination Weddings

Windy City Travel
Based on 55 reviews
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Karen Reed
Karen Reed
13:55 16 May 21
Karen is super knowledgeable. Planned a nice trip to Cancun for us!
Bryan O'Connor
Bryan O'Connor
05:30 11 Apr 21
Good service. Quick about answering usually.
Ariane Richards
Ariane Richards
01:44 14 Dec 20
Lynn hit it on the nail with our wonderful vacation. He was very responsive and amazing! I will continue to use windy... city travel for all of my future trips.read more
Philip Dalmage
Philip Dalmage
01:23 21 Apr 20
True professionals, who really listen to their clients needs. They offered a variety of options we could chose from.... Above all I appreciated the prompt and detailed communication. Amanda Hazen is awesome at finding the right place to travel. Definitely ask for her if you can.read more
Jane Farrell
Jane Farrell
17:19 26 Mar 20
Windy City Travel was very attentive to my large group and all our needs. They even got us a reservation at a... restaurant that did not take reservations! The advents fo above and beyond to provide excellent customer service. Thank you Windy City for making my spring break one I will always rememberread more
Adrienne Jones
Adrienne Jones
21:08 09 Jan 20
It was fabulous! Beautiful facilities! Good food! Great room! Wonderful, helpful, courteous staff. It was the best... vacation ever!read more
Erik Nerison
Erik Nerison
15:07 09 Jan 20
If you're looking for patient, friendly, and knowledgeable help in planning your next trip, you have found the right... place! I was lucky enough to find a good flight deal and had a month span to visit New Zealand for the first time, but I had booked my flight less than a month before I was to leave and as my departure neared, I started to panic. Moshe at WCT was kind enough to soothe my soul and talk through everyday of my 30-day itinerary with me step by step. He is a NZ expert and helped me make smart choices to smooth out my self-drive itinerary and suggested where to spend more or less time along the way. I'm extremely grateful for his patience and willingness to talk me off the ledge while making great suggestions from his expedite travelling to and booking trips in NZ. I would highly recommend both Windy City Travel and specifically Moshe for your future travel needs. Everyone in their office was kind and welcoming and eager to help in any way they can. Call here first!read more
Annabel Guzman