Northwest Side Holidays

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Top Northwest Side Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
per person
12 Jun - 14 Jun
found 23 hours ago
Return direct flight included
Providence (PVD) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Overall great experience. No complaints!!!

Reviewed on 22 Apr 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
12 Jun - 14 Jun
found 23 hours ago
Return direct flight included
Providence (PVD) to Chicago (ORD)
9/10 Wonderful! (295 reviews)
Front desk was very friendly and helpful. We had a corner unit and the view was great. The unit was very comfortable and clean.

Reviewed on 22 Apr 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
11 Jun - 15 Jun
found 1 day ago
Return direct flight included
Hong Kong (HKG) to Chicago (ORD)
9.4/10 Exceptional! (1,605 reviews)
Great breakfast every morning, the staff does a great job of making sure you enjoy the start of each day. Very walkable, its close proximity to Michigan Ave makes a trip to Chicago without a vehicle totally doable. We will be back - thank you for the great place to stay and enjoy a vacation in Chicago!

Reviewed on 24 Apr 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
11 Jun - 15 Jun
found 1 day ago
Return direct flight included
Hong Kong (HKG) to Chicago (ORD)
9.4/10 Exceptional! (1,546 reviews)
The highlight of this hotel is definitely the staff — everyone was kind, professional, and very helpful throughout our stay. Unfortunately, we did experience an issue with housekeeping, as our room wasn’t cleaned for two days. However, when I brought it to the attention of the front desk, they promptly addressed the situation and kindly removed our bar charges, which was very much appreciated. The hotel bar is one of the main attractions and definitely worth checking out!

Reviewed on 22 Apr 2025

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

Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is HK$1,206 per night from 1 May to 2 May
HK$1,206
HK$1,416 total
includes taxes & fees
1 May - 2 May
8.2/10 Very Good! (3,926 reviews)
"Nice place"

Reviewed on 23 Apr 2025

Embassy Suites by Hilton Chicago Downtown River North
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 HK$1,112 per night from 2 May to 3 May
HK$1,112
HK$1,305 total
includes taxes & fees
2 May - 3 May
7.8/10 Good! (8,694 reviews)
"I enjoyed everything"

Reviewed on 23 Apr 2025

Congress Plaza Hotel
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 HK$1,272 per night from 11 May to 12 May
HK$1,272
HK$1,493 total
includes taxes & fees
11 May - 12 May
"Nice"

Reviewed on 22 Apr 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,538 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 HK$4,591. 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

Six Flags Great America showing 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
Soldier Field featuring modern architecture, a city and a high-rise building

Soldier Field

4/5(44 reviews)

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Soldier Field
Grant Park

Grant Park

4.5/5(96 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

What to do in Northwest Side

Flyover in Chicago

Flyover in Chicago

HK$296
per adult
98% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

HK$379
per adult
94% of travellers recommend
Architecture River Tour
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

HK$346
per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge 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.