Trying to find a professional Holiday Vacation Travel Agent in Chicago, IL, to help make your next trip smooth, special, and totally worth it? That’s what we’re here for at Me and The Mouse Travel. Whether it’s Universal, Disney, or something in between, we’ll plan it from start to finish.

Get a free vacation travel quote from one of our agents, or call us at 1-855-764-2539 to start planning your next holiday getaway with our Chicago, IL, holiday vacation travel agents.

Last-minute getaway? We’ve helped families pull off unforgettable holiday vacations with just a few weeks to spare. Availability may be limited—but if there’s a way, we’ll find it.

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Learn more directly from our travelers and their guestimonials.

Why Work with a Holiday Vacation Travel Agent?

Booking a holiday trip isn’t always easy. Between timing, availability, and crowd levels, it’s a lot to juggle. Me and The Mouse Travel helps families from Chicago, IL, simplify the process. Start with our holiday travel FAQ.

As certified Disney Cruise Travel Agents and vacation planners for Universal Studios, we’ve helped thousands of families coordinate unforgettable getaways with less stress, better timing, and more value.

Our agents understand the calendar inside and out—from when crowds are lowest to when seasonal savings drop. Whether you're traveling from Chicago, IL, or beyond, we’ll help you get more from every holiday dollar.

The best part? Our holiday vacation planning services are completely free. You’ll get personalized support, expert insights, and a holiday vacation worth remembering—without adding a single dollar to your trip cost.

With first-hand experience at top destinations, our agents share helpful tips and stories on the Me and The Mouse blog.

What You Get When You Book with an Expert Chicago, IL, Holiday Travel Planner

  • Expert Advice: Get insider tips from real experiences—not reviews. Our holiday travel agents know how to help Chicago, IL families make the most of their trip.
  • Personalized Itineraries: Want rest days, early access, or fireworks every night? We’ll build the plan around it.
  • Time-Saving: Let us do the legwork so you can focus on the fun parts of the trip.
  • Exclusive Deals: We unlock upgrades, extras, and promos just for our clients.
  • Stress-Free Planning: We take care of the reservations, timing, and logistics—so you don’t have to.
  • Last-Minute Help: Emergencies, delays, or last-second changes—we’re just a call away.
  • 24/7 Backup: Around-the-clock support for anything your trip throws at you.

From theme parks to tropical ports, we help families plan unforgettable holiday trips to top destinations like Walt Disney World, Disney Cruise Line, and Universal Orlando. Each vacation style brings its own kind of holiday magic.

Chicago, IL, Holiday Travel Planners - Free Vacation Quotes

What Kind of Holiday Vacation Fits Your Family?

Some families want the magic of castle lights and character hugs. Others want beach breezes or holiday cruises. Our Chicago, IL, holiday vacation travel agents will help plan a trip that fits. Here are four of the top styles we book.

Parks

From Walt Disney World and Disneyland to Universal Orlando, the parks go all out for the holidays with seasonal parades, character events, and festivities. Great for families of all ages—especially first-time holiday travelers.

Cruises

Bring the holidays to sea with Very Merrytime Cruises from Disney Cruise Line. With festive shows, decorations, and character events, it’s a crowd favorite. We also handle seasonal trips with Royal Caribbean and Viking.

Resorts

If you’d rather swap parades for palm trees, Aulani or Disney’s holiday-themed resorts are perfect. And some cruise stops are practically floating resorts—sunny, peaceful, and just as magical.

  • Castaway Cay: This private island getaway combines beach bliss with Disney flair—from lagoon swims and bike trails to tropical drinks and Mickey-shaped snacks.
  • Lookout Cay: A fresh take on island cruising—celebrating Bahamian culture, natural beauty, and limited-access excursions only Disney can offer.

Beaches

Swap pine needles for palm fronds with a stay at Sandals or Beaches Resorts. These beachfront escapes pack holiday fun into a stress-free all-inclusive experience.

We also plan select holiday itineraries to destinations like Grand Cayman, Mexico, and Europe, where families can explore new cultures while still enjoying Disney’s signature touch.

Which Holidays (and Milestones) Are Best for a Family Vacation?

Holiday vacations can come with a lot of moving pieces—but that’s where we shine. Our team at Me and The Mouse Travel helps families plan memorable Thanksgiving, Christmas, and New Year’s getaways without the usual chaos. Reach out today for a free quote.

No matter your reason for getting away—stress relief, special occasions, or seasonal sunshine—these dates are some of the most popular we book:

  • Thanksgiving: Great for families who’d rather travel than cook. Cruises and beach resorts make it easy.
  • Christmas: One of the most magical times to travel—if you plan ahead, the payoff is huge.
  • New Year’s: Sparkling skies and stress-free escapes make this a favorite for families ready to reset.
  • Spring Break: Cruises, parks, or quick resort stays—great timing without the summer chaos.
  • Fall Break: Skip the summer chaos and enjoy cooler temps, lighter crowds, and holiday lead-ins.
  • Graduations: Big moments deserve big rewards—think cruises, resorts, or park adventures.
  • Long weekends: Make the most of quick breaks with a park visit, beach stay, or resort getaway.

If the idea of another stressful holiday makes you groan, take this as your cue to try something better.

Holiday Vacation FAQs

When should I start planning a holiday vacation?

We recommend starting 6 to 12 months in advance for any major holiday trip. It gives you first pick of resorts and cruises—and helps lock in the best dining, experiences, and prices.

Are the parks or cruises too crowded during the holidays?

The holidays bring big crowds—but also big opportunities. We’ll help you plan around the chaos with smart park days, Genie+ guidance, and just the right mix of downtime and must-dos.

What should I pack for a holiday trip?

Yes to layers. Yes to cozy outfits and Santa hats. No to overpacking. We’ll send a custom list based on your destination, so you have what you need (and nothing you don’t).

Do cruises or resorts do anything special for the holidays?

You bet. Holiday sailings and resorts don’t just decorate—they transform. Expect themed menus, limited-time shows, and festive fun at every turn. We’ll help you land the experience your family’s after.

Is it worth traveling over Christmas or New Year’s?

For a lot of families, it’s the most memorable way to spend the holidays. It does cost more, and crowds are higher—but the atmosphere, decorations, and energy are one-of-a-kind. We help you weigh the pros and cons and plan accordingly.

What if we want to celebrate the holidays while away from home?

From mini light displays to custom in-room décor, it’s easy to keep the holiday spirit alive on vacation. We’ll help you choose the best resort and festive add-ons for your family’s style.

Other trips and destination vacations we plan for Chicago travelers include:

Wherever the season takes you, our Chicago, IL, holiday travel agents are ready to help make it unforgettable.

Why Me and The Mouse? | Vacation Travel Agents for Chicago Families

Don’t wait to get a free quote from our agents at Me and The Mouse Travel to start planning your next holiday getaway. Contact us online or call 1-855-764-2539 to learn more about how our Chicago, IL, Holiday Vacation Travel Agents help families make the season magical.