Illinois Adventure Vacations
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Top Adventure vacation packages in Illinois
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Price was $234, price is now $169 per person
$169
per person
Nov 24 - Nov 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (2,874 reviews)
Hotel common areas were nice and meeting areas very convenient. The rooms were a little dated, but were fine overall.
Reviewed on Oct 24, 2025
Pendry Chicago
Downtown Chicago
Price was $640, price is now $414 per person
$414
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip flight included
Columbus (CMH) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.
Reviewed on Oct 16, 2025
The Ritz-Carlton, Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,009, price is now $703 per person
$703
per person
Dec 25 - Dec 28
found 8 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Front desk staff definitely skipped the hospitality portion of training. From the greeting to the checkout no smiles no warmth not very inviting. The hotel and room itself was beautiful, great location but most likely will go to another hotel next time.
Reviewed on Oct 24, 2025
Palmer House a Hilton Hotel
Downtown Chicago
Price was $294, price is now $218 per person
$218
per person
Dec 25 - Dec 27
found 22 hours ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
8.4/10 Very Good! (2,015 reviews)
That’s a beautiful historical hotel located in heart of Chicago. Comfortable bed, pillows, has a fridge. We loved that all the restaurants were around and it was a walking distance to Chicago Marathon start line. It would’ve been nice if they had a breakfast included, they do have a restaurant but we haven’t checked it.
Reviewed on Oct 25, 2025
InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
Price was $320, price is now $244 per person
$244
per person
Dec 25 - Dec 27
found 22 hours ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
9/10 Wonderful! (2,496 reviews)
Excellent location. Very clean
Reviewed on Oct 24, 2025
5* Adventure vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
The Ritz-Carlton, Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,009, price is now $703 per person
$703
per person
Dec 25 - Dec 28
found 8 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Front desk staff definitely skipped the hospitality portion of training. From the greeting to the checkout no smiles no warmth not very inviting. The hotel and room itself was beautiful, great location but most likely will go to another hotel next time.
Reviewed on Oct 24, 2025
The Peninsula Chicago
Downtown Chicago
Price was $1,671, price is now $1,304 per person
$1,304
per person
Dec 26 - Dec 29
found 17 hours ago
Roundtrip flight included
Charlotte (CLT) to Chicago (ORD)
9.8/10 Exceptional! (1,009 reviews)
Amazing rooms, walkable to shopping and restaurants. Great rooftop bar
Reviewed on Oct 24, 2025
Four Seasons Hotel Chicago
Downtown Chicago
Price was $1,156, price is now $969 per person
$969
per person
Dec 25 - Dec 28
found 24 hours ago
Roundtrip flight included
San Francisco (SFO) to Chicago (ORD)
9.4/10 Exceptional! (1,008 reviews)
The room was tired and neglected looking. Room service only appeared after 5 pm
Very disappointed
Reviewed on Oct 15, 2025
3 Night Adventure vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $322, price is now $213 per person
$213
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (2,874 reviews)
Hotel common areas were nice and meeting areas very convenient. The rooms were a little dated, but were fine overall.
Reviewed on Oct 24, 2025
Pendry Chicago
Downtown Chicago
Price was $640, price is now $414 per person
$414
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip flight included
Columbus (CMH) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.
Reviewed on Oct 16, 2025
The Ritz-Carlton, Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,009, price is now $703 per person
$703
per person
Dec 25 - Dec 28
found 8 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Front desk staff definitely skipped the hospitality portion of training. From the greeting to the checkout no smiles no warmth not very inviting. The hotel and room itself was beautiful, great location but most likely will go to another hotel next time.
Reviewed on Oct 24, 2025
4 Night Adventure vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Price was $448, price is now $303 per person
$303
per person
Nov 24 - Nov 28
found 11 hours ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
9/10 Wonderful! (2,874 reviews)
Hotel common areas were nice and meeting areas very convenient. The rooms were a little dated, but were fine overall.
Reviewed on Oct 24, 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $788, price is now $486 per person
$486
per person
Dec 25 - Dec 29
found 1 hour ago
Roundtrip non-stop flight included
Cincinnati (CVG) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.
Reviewed on Oct 16, 2025
The Ritz-Carlton, Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,249, price is now $837 per person
$837
per person
Dec 26 - Dec 30
found 3 hours ago
Roundtrip flight included
Lexington (LEX) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Front desk staff definitely skipped the hospitality portion of training. From the greeting to the checkout no smiles no warmth not very inviting. The hotel and room itself was beautiful, great location but most likely will go to another hotel next time.
Reviewed on Oct 24, 2025
Find awesome Illinois adventure vacations
How can I book the best Illinois adventure trips?
Choose your own adventure in Illinois, 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 Illinois family adventure vacation?
Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Illinois. 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 Illinois 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 Illinois adventure vacation for couples?
Book a Illinois 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 Illinois?
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 Illinois 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 Illinois 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.
Top Adventure Illinois Hotels
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
$130 nightly
The price is $149 total per night from Nov 24 to Nov 25
$149 total
Nov 24 - Nov 25
Total with taxes and fees
Stay at this 4-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.4/10 Very Good! (2,029 reviews)
Empty shampoo bottle for days. Hotel rooms are not as clean being an old building. The common areas are beautiful and the vibe is amazing. Easy check in and out. Great location.
Reviewed on Oct 22, 2025
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr, Chicago, IL
$199 nightly
The price is $234 total per night from Nov 23 to Nov 24
$234 total
Nov 23 - Nov 24
Total with taxes and fees
Stay at this 4-star eco-certified hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,024 reviews)
Will be back!
Reviewed on Oct 24, 2025
Hyatt Regency Chicago
151 East Wacker Dr, Chicago, IL
$164 nightly
The price is $193 total per night from Nov 24 to Nov 25
$193 total
Nov 24 - Nov 25
Total with taxes and fees
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in ...
9.2/10 Wonderful! (3,353 reviews)
Friendly staff and beautiful rooms. Felt safe to travel with my kids. Perfect 1 night stay in one of my favorite cities!
Reviewed on Oct 23, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
More vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.