Central Chicago Adventure Vacations

Book a Adventure Hotel + Flight or Car together to unlock savings

Top Adventure vacation packages in Central Chicago

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago Downtown
Hotel Riu Plaza Chicago
Trump International Hotel & Tower Chicago
Park Hyatt Chicago
Waldorf Astoria Chicago
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5* Adventure vacations in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago
Trump International Hotel & Tower Chicago
Waldorf Astoria Chicago
Don't see what you're looking for?
See all available trips from Columbus to Central Chicago
View all trips

3 Night Adventure vacations in Central Chicago

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago Downtown
Hotel Riu Plaza Chicago
Trump International Hotel & Tower Chicago
Don't see what you're looking for?
See all available trips from Columbus to Central Chicago
View all trips

4 Night Adventure vacations in Central Chicago

Price found within the past 48 hours. Click for updated prices.
The Blackstone, Autograph Collection
Level Chicago – Old Town
Hotel Riu Plaza Chicago
Don't see what you're looking for?
See all available trips from Columbus to Central Chicago
View all trips

Find awesome Central Chicago adventure vacations

How can I book the best Central Chicago adventure trips?

Choose your own adventure in Central Chicago, whether that’s a white-knuckle experience or a weekend walk. Read the reviews of the adventures that have gone before to be sure your chosen stay is your idea of fun.

How can I plan the perfect Central Chicago family adventure vacation?

Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Central Chicago. Just make sure to check your chosen escapade is within the realms of can-do for the whole clan and will have the whole team grinning.

Can I book all-inclusive Central Chicago adventure vacation packages?

By refining your filters, you can explore all-amazing, all-adventurous, all-inclusive vacation packages. Amp up the extravagance with a few more filters too. Pick pristine pools, sensational spas, or wondrous waterparks for a sensational adventure getaway.

Why should I book a Central Chicago adventure vacation for couples?

Book a Central Chicago couples adventure vacation for the ultimate in romance and memory-making. Stunning scenery, heart-racing happenings, and the grandeur of the great outdoors—it’s the best way to bond.

How can I find the best deals on adventure packages in Central Chicago?

It’s easy to unleash fabulously affordable adventures. Enter the dates for your caper, then sort your search results by price or deals.

Can I book an adventure vacation package in Central Chicago with free cancellation and/or flexible dates?

Yes! When you’re searching for a great getaway, filter by payment option for free cancellation, so a change of plans won’t mess up your adventures. You’ll find buy now, pay later options, too, for full-on flexibility.

Why should I book a Central Chicago adventure trip with Expedia?

Adventure, airfare, accommodation, ATOL protection, and activities—all on one site. And that’s just the benefits that begin with A.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.