Exclusive H.U.M. Trailhead Vacation Deals

H.U.M. Trailhead vacation package deals

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $799, price is now $409 per person
$409
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $1,362, price is now $685 per person
$685
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,021, price is now $551 per person
$551
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $876, price is now $486 per person
$486
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,169, price is now $653 per person
$653
per person
Feb 22 - Feb 26
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $756, price is now $439 per person
$439
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.

Frequently asked questions

How much are vacation packages to H.U.M. Trailhead?
Let Travelocity take the worry out of organizing your visit to H.U.M. Trailhead. Book our fantastic $409 package deal and save both time and money. With your flights and hotel sorted, you can channel your energy into planning the fun parts of your getaway — like getting to those must-see attractions!
Where can I get the best vacation package deals for H.U.M. Trailhead?
Travelocity will be able to help you find a terrific H.U.M. Trailhead package deal. With more than 400 air carriers and 1,000,000 properties around the world, we're sure you'll be able to craft the perfect itinerary.
Why should I purchase my H.U.M. Trailhead vacation bundle with Travelocity?
We offer 24/7 customer support, high-quality service and a Price Match Guarantee. Travel is all about the journey — and we have amazing destinations for you to journey to all over the world. Explore with us and your bank balance will thank you for it.

Top H.U.M. Trailhead hotel deals

AmericInn by Wyndham Woodstock IL

AmericInn by Wyndham Woodstock IL

2.5 out of 5
990 Lake Avenue Woodstock IL
Free Cancellation
Reserve now, pay when you stay
$81 nightly
The price is $90 total per night
$90 total
Dec 29 - Dec 30
Total with taxes and fees
A casino, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the indoor pool and free perks like continental breakfast and free self parking.
Pool
Breakfast included
Super 8 by Wyndham Woodstock

Super 8 by Wyndham Woodstock

2 out of 5
1220 Davis Rd Woodstock IL
Free Cancellation
Reserve now, pay when you stay
$69 nightly
The price is $76 total per night
$76 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
This motel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free on-the-go breakfast each morning. The front desk is staffed around-the-clock and free newspapers are on offer.
Breakfast included
Pet friendly
Quality Inn & Suites Woodstock near Lake Geneva

Quality Inn & Suites Woodstock near Lake Geneva

2.5 out of 5
1785 S Eastwood Dr Woodstock IL
Free Cancellation
Reserve now, pay when you stay
$68 nightly
The price is $75 total per night
$75 total
Dec 29 - Dec 30
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Parking included
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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.