Wildwood Vacations from ￥344,016

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    Save up to ￥45,448 when you book a flight and hotel together*

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The Latest Wildwood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was ￥419,975, price is now ￥344,016 per person
￥344,016
per person
Mar 22 - Mar 28
found 5 hours ago
Roundtrip flight included
Tokushima (TKS) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Perfect location, comfortable and clean room

Reviewed on Jan 5, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥565,091, price is now ￥431,406 per person
￥431,406
per person
Mar 22 - Mar 28
found 5 hours ago
Roundtrip flight included
Tokushima (TKS) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!

Reviewed on Jan 3, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was ￥581,636, price is now ￥458,678 per person
￥458,678
per person
Mar 22 - Mar 28
found 5 hours ago
Roundtrip flight included
Tokushima (TKS) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Upon check-in, it was magical! The doormen were amazing, the 'go as often as you'd like' Santa's candy shop, overall hotel decorations and the professionalism of the staff will blow you away!!! This hotel is next level up and puts the Ritz Carlton down a notch, for sure. Our room was truly magnificent and I wish we could have stayed longer!

Reviewed on Jan 6, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ￥450,266, price is now ￥368,169 per person
￥368,169
per person
Mar 22 - Mar 28
found 5 hours ago
Roundtrip flight included
Tokushima (TKS) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in

Reviewed on Dec 25, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was ￥445,109, price is now ￥367,908 per person
￥367,908
per person
Mar 22 - Mar 28
found 5 hours ago
Roundtrip flight included
Tokushima (TKS) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.

Reviewed on Dec 18, 2025

Where to stay in Wildwood

Find the best Wildwood areas and neighborhoods for the activities you enjoy most. Learn more about Wildwood
Downtown Chicago showing a city

Downtown Chicago

5 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.

Find hotels in Downtown Chicago

Wildwood Hotel Deals

Comfort Suites Grayslake near Libertyville North

Comfort Suites Grayslake near Libertyville North

2.5 out of 5
1775 East Belvidere Road Grayslake IL
Fully refundableReserve now, pay when you stay
The price is ￥14,094 per night from Jan 22 to Jan 23
￥14,094
￥15,642 total
Jan 22 - Jan 23
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
The room was clean, and the staff was friendly

Reviewed on Jan 5, 2026

Comfort Suites Grayslake near Libertyville North
Hyatt Regency Deerfield

Hyatt Regency Deerfield

4 out of 5
1750 Lake Cook Rd Deerfield IL
Fully refundableReserve now, pay when you stay
The price is ￥16,771 per night from Jan 30 to Jan 31
￥16,771
￥18,948 total
Jan 30 - Jan 31
includes taxes & fees
8.6/10 Excellent! (1,012 reviews)
Easy-to-use and good price 👌 👍

Reviewed on Jan 4, 2026

Hyatt Regency Deerfield
Motel 6 Prospect Heights, IL

Motel 6 Prospect Heights, IL

2 out of 5
540 N Milwaukee Ave Prospect Heights IL
Fully refundableReserve now, pay when you stay
The price is ￥5,722 per night from Jan 25 to Jan 26
￥5,722
￥6,409 total
Jan 25 - Jan 26
includes taxes & fees
8/10 Very Good! (1,599 reviews)
Staff friendly and courteous. Room clean and satisfactory.

Reviewed on Jan 3, 2026

Motel 6 Prospect Heights, IL
See all 802 properties in Wildwood
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 vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Wildwood from just ￥344,016. 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 vacation 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 travelers like to book hotels within easy reach of top sights, like Lake County Fairgrounds, College of Lake County and University Center of Lake County.
How far in advance should I book my Wildwood vacation?
You'll be rewarded with the widest variety at the lowest prices by booking your Wildwood vacation 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 vacation!
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 vacation package?
Yes — that's one of the best things about an Expedia vacation 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 vacation 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.

Discover the most popular places to visit in Wildwood

Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

￥6,889
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,845
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

￥6,263
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.