Wildwood Holidays from £1,543

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Your Wildwood Holiday

Take all the stress out of organising your next getaway by booking a Wildwood holiday package. Immerse yourself in the sights and sounds of this wonderful neighbourhood and experience all it has to offer. Your trip to Wildwood wouldn't be complete without seeing popular attractions nearby such as Milwaukee Avenue, Skokie Theatre and Northwestern College Chicago Campus. Expedia can put your plans into action. Book your dream Wildwood holiday now.

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £2,034, price is now £1,543 per person
£1,543
per person
30 Jul - 3 Aug
found 14 hours ago
Return flight included
London (LHR) to Chicago (ORD)
8.2/10 Very Good! (2,707 reviews)
Ordered a high floor room and it didn't really seemed like a high floor. Overall, stay did it's job and the front desk staff is amazing! Hate that Everytime I went to the bar no one was available though.

Reviewed on 17 May 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,783, price is now £1,819 per person
£1,819
per person
30 Jul - 3 Aug
found 14 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
It was very pleasant and safe. I liked that you needed a room key to use the elevator which made us feel safe. The hotel is located very central and walking distance to everything. The staff was very friendly.

Reviewed on 16 May 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was £2,481, price is now £1,809 per person
£1,809
per person
30 Jul - 3 Aug
found 14 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
Great view and room was very clean!

Reviewed on 17 May 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was £2,226, price is now £1,677 per person
£1,677
per person
30 Jul - 3 Aug
found 14 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (3,692 reviews)
The rooms are not, were not equal to the nightly amount.

Reviewed on 17 May 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £2,362, price is now £1,799 per person
£1,799
per person
30 Jul - 3 Aug
found 14 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
Great hospitality!!! Will be back! Thank you

Reviewed on 17 May 2026

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

Top hotels in Wildwood

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is £119 per night from 26 May to 27 May
£119
26 May - 27 May
includes taxes & fees
8/10 Very Good! (10,150 reviews)
Always stay here when I’m trying to save money great location and price

Reviewed on 17 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £172 per night from 26 May to 27 May
£172
26 May - 27 May
includes taxes & fees
9.4/10 Exceptional! (4,176 reviews)
The hotel was clean, staff was friendly and very helpful. My room was clean and the breakfast buffet was phenomenal. I recommend this hotel and will be a returning customer.

Reviewed on 18 May 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is £108 per night from 25 May to 26 May
£108
25 May - 26 May
includes taxes & fees
7.8/10 Good! (1,429 reviews)
I paid for room almost $600 but Expedia didn’t send me breakfast.

Reviewed on 18 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,812 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.
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Frequently asked questions

How much does a Wildwood travel package cost?
Less than you might think — from just £1,543, as a matter of fact! By combining flights, hotels and car rentals into a custom-built travel package, your getaway to Wildwood is just a few clicks away.
If I'm not able to travel, can I cancel my Wildwood travel package?
If your holiday plans in Wildwood have changed, it's good to know that it's possible to cancel or amend your booking. If your booking was made less than 24 hours ago, you may be eligible for a refund. If your booking is older than that, your airline, hotel or car rental company may impose a fee. To find out more, check our Customer Service Portal.
How do I get a cheap travel package to Wildwood?
Just think of all the awesome things you could do in Wildwood with extra cash in your pocket. Watch your savings stack up when you combine your hotel and flights into a Wildwood travel package. You have loads of choice when you book your trip with Expedia too. In fact, you can take your pick of more than 550 air carriers and 1,000,000 properties around the world. Whether you're enjoying a break with the family or going it alone, organising a trip to Wildwood is better with a package.
Does Expedia offer Book Now, Pay Later Wildwood holidays?
Your bank balance shouldn't get in the way of escaping on holiday, so Expedia has worked out a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book a fantastic getaway without exhausting your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your escape. Consider one of these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month works for you, Klarna can help. Paying in convenient monthly instalments will make that dream getaway possible.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay for your holiday across multiple transactions.
  • Low deposit holidays: Clicking on the "book now" button is much easier with this plan. Just put down a small deposit on your escape and then start working on your travel plans.

Where should I stay in Wildwood?
Make sightseeing easier by staying in a hotel just around the corner from Wildwood's big attractions. Millennium Park and Wrigley Field are two visitor favourites.
What are the top hotels in Wildwood?
Get your escape off to a flying start by staying at Hyatt Regency Chicago. It's one of most popular properties in Wildwood. Another welcoming option is The Godfrey Hotel Chicago.
How far in advance should I book my Wildwood holiday?
Savvy travellers often reserve their seats as early as possible. You can generally browse through international fares on Expedia up to 12 months before your flight. If you're purchasing your ticket at the last minute, there's no need to worry. Discounted prices sometimes become available in the last weeks prior to departure.
What does an Expedia Wildwood travel package include?
Flights, hotels and a reliable car for your road trip adventures. Simply pick and choose your preferred bundle and gain access to great discounts. Once you've made your booking, add on a couple of tours and experiences and watch your savings pile up. When it comes to planning your Wildwood holiday, you're in charge!
What should I know before booking a Wildwood travel package?
Bundling your bookings into a Wildwood travel package is the easiest way to organise your trip. Not only that, you'll save just for combining your flights, hotels and car rentals. Once you've booked, why not add on a tour or an activity?
Can I choose my airline with a Wildwood Expedia travel package?
Yes, so take your pick! We offer more than 550 partner airlines worldwide, so you can design your Wildwood escape according to your needs and budget.

Popular places to visit

Wrigley Field

Wrigley Field

4.5/5(40 reviews)

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

Wrigley Field
Navy Pier

Navy Pier

4/5(127 reviews)

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

Navy Pier
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home 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

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

£16
per child
98% of travellers recommend
Flyover in 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. Flight-inclusive packages are ATOL protected.