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
WCT Banner Ad

TSA Pre-Check Temporary Enrollment Center Event

You don’t need to head to the airport and wait in a long line to enroll in TSA PreCheck. Our Windy City Travel office is excited to be a host for a pop-up enrollment event.

June 6 – 10, 2022

Windy City Travel – 1357 N. Wells St. Chicago 60610

Click for details
Windy City Travel 2022 6 TSAPreCheck Pop up events 1080x1920 Page 2

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 66 reviews
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Merrilynn Martin
Merrilynn Martin
13:09 20 Apr 22
Karen at Windy City Travel is AMAZING!!!! She solves all challenges and creates an ease to your vacation. I have... referred her to many friends and family and everyone raves about her. There is nothing she can't do!!read more
Patricia Jackson
Patricia Jackson
22:36 29 Mar 22
Had a wonderful experience with Lynn Farrel planning a trip for my family to Punta Cana. Very professional. Trip was... great… will definitely use Windy City Travel againread more
Megan Seil
Megan Seil
03:06 23 Mar 22
I sent an inquiry for a European trip and got a phone call back from one of their agents. I had a nice, somewhat long... and in-depth, call which ended with a promise of a return call with a loose itinerary of my future trip. I never heard back from this agent. I found this to be very frustrating because she took my time and promised a return call which I never received. I would not recommend this agent for that reason. I ended up booking my trip online at tripmasters which saved me a lot of money and I had a perfect vacation. I only wish I wouldn't have wasted time booking the trip waiting for a response from Windy City travel.read more
Evan Huss
Evan Huss
22:40 21 Mar 22
I came across this site and was paired with Sandi- She did an amazing job! I am a senior in college, and I was in... charge of figuring out a cheap/fun spring break trip. She found the perfect trip that was in our budget! She also was great at responding quickly when we had questions and issuesread more
Yoseph Sarsour
Yoseph Sarsour
18:26 27 Feb 22
Amanda is the best. She answered every question and made the whole process very easy. My wife and I look forward to... working with her in the near future.read more
Rob O'Doherty
Rob O'Doherty
02:46 30 Nov 21