Illinois Adventure Vacations
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Top Adventure vacation packages in Illinois
Price found within the past 48 hours. Click for updated prices.
Warwick Allerton - Chicago
Downtown Chicago
Price was $732, price is now $612 per person
$612
per person
Jun 6 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Chicago (ORD)
8.6/10 Excellent! (3,032 reviews)
A beautiful historic hotel...we very much enjoyed our stay there.
Reviewed on Mar 31, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $989, price is now $785 per person
$785
per person
May 6 - May 9
found 5 hours ago
Roundtrip flight included
Tampa (TPA) to Chicago (ORD)
9.4/10 Exceptional! (3,647 reviews)
Clean room! The view was amazing
Reviewed on Apr 6, 2026
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Downtown Chicago
Price was $1,164, price is now $930 per person
$930
per person
Jun 6 - Jun 9
found 16 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
8.2/10 Very Good! (2,828 reviews)
Staff was friendly, welcoming and helpful. Room was ready promptly and was very clean and comfortable. Breakfast was great, and even though it was very busy during spring break, staff did a great job accommodating the crowd by constantly cleaning tables and refreshing food.
My only marks against the stay are that the pool was closed one of the days, and the elevators were being worked on, so there was often a line and a wait to use them. But the staff warned us about it upon check-in, so that made it more bearable.
Reviewed on Apr 5, 2026
Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
Price was $1,028, price is now $843 per person
$843
per person
Jun 11 - Jun 14
found 2 hours ago
Roundtrip non-stop flight included
Austin (AUS) to Chicago (ORD)
8.6/10 Excellent! (5,808 reviews)
It was great. I just wish the food better.
Reviewed on Apr 5, 2026
5* Adventure vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
Price was $1,757, price is now $1,645 per person
$1,645
per person
Jun 6 - Jun 9
found 16 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Service was wonderful! Hotel is very well located close to shops, restaurants and coffee shops. Lots to see and do around and hotel itself is pure luxury. We had a wonderful stay!
Reviewed on Mar 27, 2026
The Peninsula Chicago
Downtown Chicago
Price was $1,248, price is now $1,170 per person
$1,170
per person
May 6 - May 8
found 1 day ago
Roundtrip flight included
Salt Lake City (SLC) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
Excellent room and facilities. Helpfull staff and amazing locstion.
Reviewed on Mar 27, 2026
3 Night Adventure vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago - Magnificent Mile
Downtown Chicago
Price was $915, price is now $701 per person
$701
per person
Jun 9 - Jun 12
found 2 hours ago
Roundtrip flight included
New Orleans (MSY) to Chicago (ORD)
8.8/10 Excellent! (2,391 reviews)
Great rooms. The beds were very comfortable and the buffet breakfast was one of the nicest I’ve had in a US hotel in a while. I do wish they would just make regular chocolate chip cookies though stop adding nuts. I really love the warm chocolate chip cookies from the Doubletree.
Reviewed on Apr 4, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,033, price is now $749 per person
$749
per person
Jun 10 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Chicago (ORD)
9.4/10 Exceptional! (3,647 reviews)
Clean room! The view was amazing
Reviewed on Apr 6, 2026
4 Night Adventure vacations in Illinois
Price found within the past 48 hours. Click for updated prices.
Riverview Inn & Suites, an Ascend Collection Hotel
Price was $757, price is now $592 per person
$592
per person
Jun 19 - Jun 23
found 23 hours ago
Roundtrip non-stop flight included
Boise (BOI) to Chicago (ORD)
8.4/10 Very Good! (1,004 reviews)
This hotel is my family's favorite place to stay when we come to Rockford. The staff has always been incredible, friendly, and professional. The rooms are different from any other hotel we've stayed in. We always stay in the suites and my wife and I sleep upstairs and our son sleeps downstairs. The amount of charm and uniqueness is what will always bring us back. The pool is smaller but there is a pool. Same with the gym but these aren't things that are too important for us.
Reviewed on Apr 5, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,311, price is now $861 per person
$861
per person
Jun 10 - Jun 14
found 1 day ago
Roundtrip flight included
Rochester (RST) to Chicago (ORD)
9.4/10 Exceptional! (3,647 reviews)
Clean room! The view was amazing
Reviewed on Apr 6, 2026
Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
Save 100% on your flight
Price was $1,119, price is now $863 per person
$863
per person
Jun 11 - Jun 15
found 2 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Chicago (ORD)
8.6/10 Excellent! (5,808 reviews)
It was great. I just wish the food better.
Reviewed on Apr 5, 2026
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
$209 nightly
The price is $241 total per night from Apr 26 to Apr 27
$241 total
Apr 26 - Apr 27
Total with taxes and fees
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.6/10 Excellent! (2,356 reviews)
The hotel main lobby is so beautiful! The pool was great and warm for the cold weather. Everything is walking distance.
Reviewed on Apr 3, 2026
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
$210 nightly
The price is $247 total per night from May 7 to May 8
$247 total
May 7 - May 8
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,073 reviews)
Place was nice as always. We always go for a convention. Room was newly renovated. Trhe bathroom light wouldnt stay on though. It was on a timer and if you were in the shower it would just click off and youd be lift in darkness. Staff was okay for the most part besides the bell hop. Husband tried ...
Reviewed on Mar 30, 2026
Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
$279 nightly
The price is $328 total per night from Apr 7 to Apr 8
$328 total
Apr 7 - Apr 8
Total with taxes and fees
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (3,477 reviews)
This hotel is great! Great location, great staff.
Reviewed on Apr 3, 2026
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.
