Wildwood Vacations from ￥188,740

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The Latest Wildwood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was ￥272,410, price is now ￥188,740 per person
￥188,740
per person
Nov 12 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
Nice hotel but room was extremely small.

Reviewed on Sep 11, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ￥460,254, price is now ￥301,832 per person
￥301,832
per person
Nov 12 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Great bar on the 16th floor. Staff was great

Reviewed on Sep 10, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥314,632, price is now ￥221,254 per person
￥221,254
per person
Nov 12 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,373 reviews)
Rooms are very clean and staff was great

Reviewed on Sep 11, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was ￥321,014, price is now ￥236,332 per person
￥236,332
per person
Nov 12 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,070 reviews)
The property is gorgeous! Lovely rooms and the staff were fantastic, could not fault them at all! My only issue would be the roads outside are very noisy, we needed ear plugs to sleep. Other than that, absolutely fantastic stay! Would return and would highly recommend

Reviewed on Sep 8, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was ￥282,136, price is now ￥210,421 per person
￥210,421
per person
Nov 12 - Nov 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,014 reviews)
First time but won’t be the last. Very nice place with lots to do right around there.

Reviewed on Sep 9, 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

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 ￥17,518 per night from Sep 26 to Sep 27
￥17,518
￥19,791 total
Sep 26 - Sep 27
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
"The place was quiet and convenient to the airport."

Reviewed on Sep 9, 2025

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 ￥6,292 per night from Oct 2 to Oct 3
￥6,292
￥7,047 total
Oct 2 - Oct 3
includes taxes & fees
8/10 Very Good! (1,381 reviews)
"Pretty good for the price"

Reviewed on Sep 5, 2025

Motel 6 Prospect Heights, IL
Embassy Suites by Hilton Chicago North Shore Deerfield

Embassy Suites by Hilton Chicago North Shore Deerfield

4 out of 5
1445 Lake Cook Rd, Deerfield, IL
Fully refundableReserve now, pay when you stay
The price is ￥21,147 per night from Sep 21 to Sep 22
￥21,147
￥24,104 total
Sep 21 - Sep 22
includes taxes & fees
8.8/10 Excellent! (1,233 reviews)
"Easy check in. Quiet location Enjoyed the stay"

Reviewed on Sep 9, 2025

Embassy Suites by Hilton Chicago North Shore Deerfield
See all 682 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 ￥188,740. 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

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
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
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

River tour boat in Chicago

Architecture River Tour

￥7,240
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥6,681
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

￥6,681
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
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.