Waukegan Holidays

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Top Flight + Hotel Deals in Waukegan

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 €1,199, price is now €792 per person
€792
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Everything was nice!!

Reviewed on 23 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €1,918, price is now €1,155 per person
€1,155
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was €1,420, price is now €868 per person
€868
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on 22 Aug 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was €1,979, price is now €1,240 per person
€1,240
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was €1,917, price is now €1,272 per person
€1,272
per person
2 Nov - 9 Nov
found 17 hours ago
Return direct flight included
Faro (FAO) to Chicago (ORD)
9.4/10 Exceptional! (1,059 reviews)
Will be coming back! Beautiful rooms and great staff.

Reviewed on 24 Aug 2025

Top hotels in Waukegan

Sonesta ES Suites Chicago Waukegan Gurnee

Sonesta ES Suites Chicago Waukegan Gurnee

3 out of 5
1440 S White Oak Dr, Waukegan, IL
Fully refundableReserve now, pay when you stay
The price is €99 per night from 2 Sept to 3 Sept
€99
2 Sept - 3 Sept
includes taxes & fees
8.8/10 Excellent! (1,318 reviews)
"Hotel not new but clean and well cared for. Friendly staff and good amenities"

Reviewed on 22 Aug 2025

Sonesta ES Suites Chicago Waukegan Gurnee
Courtyard Chicago Waukegan Gurnee

Courtyard Chicago Waukegan Gurnee

3 out of 5
3800 Northpoint Blvd, Waukegan, IL
Fully refundableReserve now, pay when you stay
The price is €139 per night from 31 Aug to 1 Sept
€139
31 Aug - 1 Sept
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"Great experience"

Reviewed on 21 Aug 2025

Courtyard Chicago Waukegan Gurnee
Red Roof Inn Gurnee - Waukegan

Red Roof Inn Gurnee - Waukegan

2 out of 5
3031 Belvidere Rd, Waukegan, IL
Fully refundableReserve now, pay when you stay
The price is €76 per night from 1 Sept to 2 Sept
€76
1 Sept - 2 Sept
includes taxes & fees
7/10 Good! (1,003 reviews)
"Arrived cery late, service was excellent, he was out to help us before we rang the bell!! Comfortable bed. Pillows were flat but overall decent place at a decent price."

Reviewed on 7 Aug 2025

Red Roof Inn Gurnee - Waukegan
See all 684 properties in Waukegan
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.

Popular places to visit

Wrigley Field featuring central business district, a city and a sporting event

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
Magnificent Mile - River North showing street scenes, signage and night scenes

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
Navy Pier

Navy Pier

4/5(125 reviews)

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

Navy Pier

What to do in Waukegan

River tour boat in Chicago

Architecture River Tour

€36
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

€35
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

€39
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Waukegan

Frequently asked questions

How much does a Waukegan holiday package cost?
You can snap up a holiday package to this top destination from €792 on Expedia. However, how much your holiday to Waukegan costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Waukegan?
You can generally find lower prices and better availability in February, March and December. Take a look at our cheap Waukegan holiday packages and you could land some great off-season discounts.
How many days is enough for Waukegan?
With a well-planned itinerary, you can easily visit the top Waukegan sights in a handful of days. But if you prefer to discover lesser-known spots or go on day trips, think about booking your Waukegan holiday for longer.
Is it worth booking a holiday package to Waukegan?
Known for its history, culture and a host of other highlights, you can be assured Waukegan is a good holiday destination. Some of the most popular attractions to put on your to-do list? Don't miss Genesee Theatre and Bonnie Brook Golf Course during your Waukegan holiday.
How to find the best Waukegan package deals?
Landing a cheap Waukegan package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget range, add some filters and browse what's available. You can tailor your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Waukegan package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Waukegan holiday as a package?
An Expedia holiday package could land you great savings when compared to arranging flights and accommodation individually. Better still, you can tailor your Waukegan getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Waukegan?
If you've got your Waukegan travel dates locked in, book early to snap up some terrific deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for travelling on a whim.
How to plan a trip to Waukegan?

  1. Choose when to go: Check your diary and get your bags packed. Your favourite season and the type of activities on offer will also help you decide when to holiday in Waukegan.
  2. Work out your budget: Make sure you have enough money to pay for everything from food and transportation to airfares and activities. Your accommodation will probably be the biggest expense during your trip to Waukegan.
  3. Set the duration of your trip: Start by making a list of all the activities and attractions you want to get to in Waukegan. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a personalised Waukegan holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.