Wildwood Holidays

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  • Better together

    Save up to NZ$2,400 when you book a flight and hotel together*

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Price found within the past 48 hours. Click for updated prices.
  • Lobby lounge
    Aug 14 - Aug 16

    Le Méridien Essex Chicago + Flight

    Downtown Chicago
    2 nights
    4.0 star property
    9.0/10 - Wonderful (1,003 reviews)
    "Would definitely stay here again! Clean, friendly staff, great location."
    Reviewed May 23, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • Direct ORD - JFK • Direct
    NZ$999
    NZ$787
    per traveller
    found 1 day ago
    Le Méridien Essex Chicago
  • Lobby
    Aug 14 - Aug 16

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    2 nights
    4.0 star property
    8.2/10 - Very good (2,717 reviews)
    "Too small room no refrigerator no microwave over prized vallet parking when they park in open public parking space which cost less."
    Reviewed May 23, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • Direct ORD - JFK • Direct
    NZ$1,164
    NZ$878
    per traveller
    found 1 day ago
    Hotel Felix River North/Magnificent Mile
  • Executive lounge
    Aug 14 - Aug 16

    Fairmont Chicago at Millennium Park + Flight

    Downtown Chicago
    2 nights
    4.5 star property
    8.8/10 - Excellent (2,165 reviews)
    "Amazing staff. Clean rooms!"
    Reviewed May 21, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • Direct ORD - JFK • Direct
    NZ$1,127
    NZ$859
    per traveller
    found 1 day ago
    Fairmont Chicago at Millennium Park
  • 55-inch LCD TV with cable channels, TV, pay films
    Aug 14 - Aug 16

    L7 Chicago by LOTTE + Flight

    Downtown Chicago
    2 nights
    4.5 star property
    9.6/10 - Exceptional (4,081 reviews)
    "Upon check-in, Alex was kind and helpful. He gave us some great tips about the hotel and some things to explore and where to eat. Alex was moved by our mother-daughter trip before my daughter travels to Spain to study. He even left us a sweet treat which was a perfect end to our evening. The room, the view, and the shower were absolutely perfect! We will be back to Chicago and because of Alex we will only be staying at L7 when we do. Thanks for your kind words, Alex."
    Reviewed May 24, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • Direct ORD - JFK • Direct
    NZ$1,106
    NZ$885
    per traveller
    found 1 day ago
    L7 Chicago by LOTTE
  • Indoor wedding
    Aug 14 - Aug 16

    Swissotel - Chicago + Flight

    Downtown Chicago
    2 nights
    4.5 star property
    9.0/10 - Wonderful (3,337 reviews)
    "Great location!"
    Reviewed May 23, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • Direct ORD - JFK • Direct
    NZ$1,201
    NZ$964
    per traveller
    found 1 day ago
    Swissotel - Chicago

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

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

Our pick of the best 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 refundable
The price is NZ$178 per night from 31 May to 1 June
NZ$178
31 May - 1 June
includes taxes & fees
8.4/10 Very Good! (1,005 reviews)
"This is the place to go when you need a break from the hustle/busle of big city life."

Reviewed on 24 May 2026

Comfort Suites Grayslake near Libertyville North
Baymont by Wyndham Glenview

Baymont by Wyndham Glenview

3 out of 5
1625 Milwaukee Ave Glenview IL
Fully refundableReserve now, pay when you stay
The price is NZ$130 per night from 31 May to 1 June
NZ$130
31 May - 1 June
includes taxes & fees
Baymont by Wyndham Glenview
Great Wolf Lodge Illinois

Great Wolf Lodge Illinois

3 out of 5
1700 Nations Dr Gurnee IL
Fully refundableReserve now, pay when you stay
The price is NZ$319 per night from 26 May to 27 May
NZ$319
26 May - 27 May
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
"Clean room. Extremely friendly and helpful staff. Very family friendly. Overall a great experience."

Reviewed on 23 May 2026

Great Wolf Lodge Illinois
See all 815 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 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.

Discover the most popular places to visit in Wildwood

Wrigley Field

Wrigley Field

A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Navy Pier

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$45
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

NZ$74
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

NZ$77
per adult
100% of travellers recommend
Chicago Sightseeing River and 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.