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 58 reviews
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Rob O'Doherty
Rob O'Doherty
02:46 30 Nov 21
I'm literally obsessed with Lynn and Windy City Travel.Lynn is fabulous to work with, super knowledgeable and has... great recommendations. My husband and I just got back from our 'mini honeymoon' in Cancun and the adults only resort that Lynn recommended based on what we asked for was a perfect match.We're also currently working with Lynn on booking Italy and Greece for Summer of 2022! She and her team at Windy City Travel are our new go to's for sure!read more
Letitia Powell
Letitia Powell
01:38 12 Aug 21
I've been working and rocking with Karen Murdock since 2018, when she planned our getaway to Dominican Republic. We... stayed at a newly open all inclusive resort called Hotel Chic, and it was amazing! It feels like she knows me and my traveling needs to the tee, and she has never disappoints. She's always professional, and does not miss any details from the transportation, to all the incentives the resort has to offer ensuring we're treated wonderful and are comfortable our entire stay. Karen can book me a vacation anywhere, anytime. Thank you Karen for always being available and meeting my needs. #StangGangread more
Camille Clark
Camille Clark
01:11 12 Aug 21
Karen Murdock was wonderful.She has worked with my High school class on numerous trips and we all love her. She is... very professional and responds to questions or concerns in a timely manner. We just returned from Cancun and she was on top of everything. I would definitely recommend Windy City Travel and choose Karen.read more
Brandee Stanton
Brandee Stanton
19:45 11 Aug 21
Karen Murdock has been our dedicated travel agent for a few years now. We had a group of 14 to Cancun, Mexico at the... new Planet Hollywood Resort early August 2021 and our experience was phenomenal! Any hiccups encountered during our check in and stay were taken care of immediately, no back and forth needed. Not only that, she happened to be near the resort and came to meet us IN PERSON and brought us goodie bags! You won't find better professionalism, attention to detail and service any where else!read more
Celeste Kearney
Celeste Kearney
12:07 04 Aug 21
Karen Murdock is very unprofessional. Karen do not return phone calls she give false information. She lack whole lot of... poor quality. I will not promote her business or give any referrals. I give NOOOOOOOOOOOOOO Stars to her.read more
eric jones
eric jones
15:59 07 Jul 21
Windy City Travel was exactly what I was looking for when planning my vacation. Being able to simply pick up the phone,... talk to an agent who took care of booking my flights, car rental, and hotel in the area I wanted was so convenient, and all at reasonable price. I was able to relax immediately and enjoy the excitement looking forward to my trip. I will certainly use Windy City Travel for future trips.read more
Karen Reed
Karen Reed
13:55 16 May 21
Karen is super knowledgeable. Plann