Northwest Side Holidays

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Where to stay in Northwest Side

Find the best Northwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Northwest Side
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Irving Park

2 out of top 10 points of interest in this area

Appreciated for its restaurants and live music, you might consider exploring Irving Park. Check out the variety of things to see and do like Milwaukee Avenue, and jump on the metro at Irving Park Station (Blue Line) or Montrose Station (Blue Line) to get around the city.

Find hotels in Irving Park

Top hotels in Northwest Side

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 S$216 per night from 3 Jul to 4 Jul
S$216
includes taxes & fees
3 Jul - 4 Jul
7.8/10 Good! (8,814 reviews)
"The hotel is conveniently locate on the Millennium Mile. The staff is very friendly and the room was clean."

Reviewed on 2 Jun, 2025

Congress Plaza Hotel
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$185 per night from 1 Jul to 2 Jul
S$185
includes taxes & fees
1 Jul - 2 Jul
9.2/10 Wonderful! (3,135 reviews)
"Greatness"

Reviewed on 3 Jun, 2025

citizenM Chicago Downtown
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$247 per night from 30 Jun to 1 Jul
S$247
includes taxes & fees
30 Jun - 1 Jul
8.8/10 Excellent! (2,270 reviews)
"Beautiful space, right near the lake. Also has a cozy little restaurant on the 1st floor"

Reviewed on 3 Jun, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,832 properties in Northwest Side
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 Northwest Side holiday package cost?
Explore the best of Northwest Side from just . Choose from a great selection of rental cars, hotels and flights to suit every budget. Land even better deals when you add a few experiences or tours to your package.
How do I get a cheap travel package to Northwest Side?
Book everything all in one place with our Northwest Side holiday packages. We have deals on flights, hotels, tours and more that’ll keep your pocketbook happy and your sense of adventure alive. And, with more than 550 air carriers and 1,000,000 hotel options globally to choose from, you’ll have the flexibility to mix and match as you like.
How far in advance should I book my Northwest Side holiday?
Savvy travellers often reserve their seats early. You can generally look up international airfares on Expedia up to a year before your intended flight. If you’re late to book, don’t despair. Low prices occasionally become available just weeks prior to departure.
What does an Expedia Northwest Side travel package include?
Hotels, rental cars and flights, or any combination of the three — you decide! Whether you’re headed to Northwest Side on a family road trip or travelling solo, there’s a package to fit every budget and style. Once you’ve made your booking, why not add on some activities?
Can I choose my airline with a Northwest Side Expedia holiday package?
Yes — and it’s simple too. Expedia has access to more than 550 partner airlines worldwide. Our holiday packages give you the flexibility to pick from available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Northwest Side holiday package?
Because we understand life is full of surprises, the answer is yes. To find out more, head to our Customer Service Portal. But generally speaking, if you’ve booked your package in the last 24 hours, you may be able to change or cancel it for no charge. Your airline, hotel or car rental company may impose a fee if your booking is older than that.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

4.5/5(40 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
Six Flags Great America which includes rides

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America
McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place

What to do in Northwest Side

River tour boat in Chicago

Architecture River Tour

S$63
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

S$58
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

S$31
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Northwest Side

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.