Waukegan Holidays

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Top Flight + Hotel Deals in Waukegan

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Loved the old time and modern vibe.

Reviewed on 9 Aug 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
This was my first time staying. The staff was very friendly and helpful. Our room was very nice and perfectly located downtown. Also, the breakfast buffet was amazing and a nice surprise.

Reviewed on 9 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
Really nice and amazing location!! Would stay again!

Reviewed on 9 Aug 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (332 reviews)
A lot of good food options walkable distance.

Reviewed on 3 Aug 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (1,991 reviews)
I liked this hotel, the rooms are cleaning and beautiful, the staff is nice, and the hotel is located near amazing restaurants, cafes, and tourist places.

Reviewed on 9 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
The price is €100 per night from 2 Sept to 3 Sept
€100
2 Sept - 3 Sept
includes taxes & fees
8.8/10 Excellent! (1,281 reviews)
"Excellent"

Reviewed on 6 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 24 Aug to 25 Aug
€139
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
"My favorite hotel tbh"

Reviewed on 8 Aug 2025

Courtyard Chicago Waukegan Gurnee
Sonesta Simply Suites Chicago Waukegan

Sonesta Simply Suites Chicago Waukegan

2 out of 5
1151 S Waukegan Rd, Waukegan, IL
Fully refundableReserve now, pay when you stay
The price is €82 per night from 2 Sept to 3 Sept
€82
2 Sept - 3 Sept
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
"Great!!"

Reviewed on 1 Aug 2025

Sonesta Simply Suites Chicago Waukegan
See all 712 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

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

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

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
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

€39
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
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 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 €805 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.