Wildwood Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Our guide on where to stay in Wildwood
Find the best Wildwood areas and neighborhoods for the activities you enjoy most. Learn more about Wildwood
Downtown Chicago
4 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Magnificent Mile
An avenue brimming with superb shops and restaurants, the Magnificent Mile more than lives up to its name.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Our pick of the best Wildwood Hotel Deals
Comfort Suites Grayslake near Libertyville North
1775 East Belvidere Road Grayslake IL
Fully refundable
NZ$176
1 Nov - 2 Nov
includes taxes & fees
Hyatt Regency Deerfield
1750 Lake Cook Rd Deerfield IL
Fully refundableReserve now, pay when you stay
NZ$254
1 Nov - 2 Nov
includes taxes & fees
8.8/10 Excellent! (1,259 reviews)
"We were extremely disappointed with the service we received at this hotel. Our check-out was scheduled for noon. We went downstairs for breakfast around 9:00 a.m., and when we returned around 10:00 a.m., we found that the bed sheets, pillowcases, and towels had already been removed from the room, ..."
Reviewed on 7 Oct 2026
Motel 6 Rolling Meadows, IL - Chicago Northwest
1800 Winnetka Cir Rolling Meadows IL
Fully refundableReserve now, pay when you stay
NZ$109
14 Oct - 15 Oct
includes taxes & fees
7.2/10 Good! (1,448 reviews)
"Lots of parking good for a night of sleep. It’s in between like warehouses so pretty quiet area"
Reviewed on 7 Oct 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.
Frequently asked questions
How much does a Wildwood holiday package cost?
Choose from any combination of hotels, flights and car rentals, and you can be holidaying in Wildwood from just . And the more you bundle, the more dollars you save. The getaway of your dreams has never been more affordable.
How do I get a cheap travel package to Wildwood?
Browse and lock in everything all in one place with our Wildwood holiday packages. You'll discover bargains on hotels, flights and more that'll keep your wallet happy and adventurous side satisfied. And, with more than 550 airlines and 1 000 000 hotel options throughout the world to select from, you'll have the flexibility to mix and match your own way.
Where should I stay in Wildwood?
Stay where the action happens. Many travellers like to book hotels within easy reach of top sights, like Lake County Fairgrounds, College of Lake County and University Centre of Lake County.
How far in advance should I book my Wildwood holiday?
You'll be rewarded with the widest variety at the lowest prices by booking your Wildwood holiday early. Airlines usually publish flight tickets anywhere up to 12 months in advance, so start locking things in ASAP. Having said that, Expedia is committed to giving you the best deals around, so it's never a bad time to book your dream holiday!
What does an Expedia Wildwood travel package include?
It depends on what kind of escape you want to have. Wildwood travel deals can include car rentals, hotels and flights. You can mix and match to create the package that works for you! You can also add on experiences and activities after you've booked to land even bigger discounts.
What should I know before booking a Wildwood travel package?
Our prices are already low. However, you'll pick up even more savings if you book your flights, hotels and car rentals together. With an Expedia package, you'll always get transparent pricing and lots of choice.
Can I choose my airline with a Wildwood Expedia holiday package?
Yes — that's one of the best things about an Expedia holiday package. You're the boss! We have more than 550 partner airlines around the world, so you have lots of choice when putting together your Wildwood adventure.
If I'm not able to travel, can I cancel my Wildwood holiday package?
It is possible to cancel your Wildwood booking if your plans have changed. Whether you'll incur a penalty or not depends on your airline, hotel or car rental company. You may be able to cancel or change free of charge if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.
Activities
Skydeck Chicago at Willis Tower
NZ$74
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.