Northwest Side Vacations from ￥250,434

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The Latest Northwest Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
Sep 16 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,785 reviews)
The servers and bartenders at the property were amazing! Gentleman who stored our luggage was polite and extremely attentive!

Reviewed on Jul 16, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Excellent stay - outstanding Director of Rooms and valet staff made my daughters wedding an amazing experience - just outstanding !!

Reviewed on Jul 16, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 16 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Superb customer service, clean hotel!

Reviewed on Jun 13, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Beautiful boutique hotel in the heart of Chicago with exceptional customer service.

Reviewed on Jul 16, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
Sep 16 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I loved the location of the property, and the overall concept of something fun and funky, but I had a "higher end" room, and it was right near the elevator, so I got a lot of noise on that side, plus the El from the other side. The rug wasn't super clean (although the bedding and the rest of the room were a delight). The most annoying thing was the TV. Anything I turned it to, 10 minutes later to the minute, it went back to the Virgin channel #1, here are all our hotels in the world. I really hated having to stay on top of a show, when usually I want the tv on as background while I'm getting ready, etc. Also, this hotel's amenities were oversold, i.e., good luck getting on the rooftop, especially if you just wanted a quiet sip of a drink. I loved the cafe and the staff, though, everyone was very pleasant.

Reviewed on Jul 15, 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
4/5(1 area review)

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

Find the Best Northwest Side Vacation Packages

Northwest Side Hotel Deals

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 ￥21,859 per night from Aug 5 to Aug 6
￥21,859
￥25,661 total
Aug 5 - Aug 6
includes taxes & fees
7.8/10 Good! (8,985 reviews)
"Historic hotel!"

Reviewed on Jul 16, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is ￥31,448 per night from Aug 10 to Aug 11
￥31,448
￥41,681 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (2,048 reviews)
"8lmicr"

Reviewed on Jul 16, 2025

InterContinental Chicago Magnificent Mile by IHG
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 ￥21,896 per night from Aug 10 to Aug 11
￥21,896
￥25,702 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (2,445 reviews)
"Good"

Reviewed on Jul 15, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,900 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.

Discover the most popular places to visit in Northwest Side

Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

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

Wrigley Field
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

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

Navy Pier
Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 reviews)

You can enjoy some retail therapy 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

What to do in Northwest Side

River tour boat in Chicago

Architecture River Tour

￥7,149
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

￥6,597
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

￥6,597
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Northwest Side

Frequently asked questions

How much does a Northwest Side vacation package cost?
Explore the best of Northwest Side from just ￥250,434. 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 vacation 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 vacation?
Savvy travelers 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 traveling 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 vacation package?
Yes --- and it's simple too. Expedia has access to more than 550 partner airlines worldwide. Our vacation 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 vacation 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.