Northwest Side Vacations from ￥295,012

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The Latest Northwest Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Buckingham Hotel

The Buckingham Hotel

3.5 out of 5
Downtown Chicago
Price was ￥337,531, price is now ￥295,012 per person
￥295,012
per person
Sep 18 - Sep 22
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,003 reviews)
The view from our suite was excellent, especially during a thunderstorm. We loved our stay. The only (very minor) downside was neither TV worked correctly. One had very low volume, the other had no picture but good volume. The location was very good, very easy walk to public transportation. The room was clean, the bed was comfortable, and the A/C worked really well. The building security was Would definitely stay here again.

Reviewed on Jul 11, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was ￥379,612, price is now ￥309,040 per person
￥309,040
per person
Sep 18 - Sep 22
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,764 reviews)
No

Reviewed on Jul 11, 2026

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Downtown Chicago
Price was ￥366,988, price is now ￥312,042 per person
￥312,042
per person
Sep 18 - Sep 22
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (3,123 reviews)
Good value.

Reviewed on Jul 11, 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Price was ￥370,063, price is now ￥321,758 per person
￥321,758
per person
Sep 18 - Sep 22
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,429 reviews)
The staff was super friendly and helpful

Reviewed on Jul 10, 2026

The Wade

The Wade

4.5 out of 5
Downtown Chicago
Price was ￥348,343, price is now ￥305,115 per person
￥305,115
per person
Sep 18 - Sep 22
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (1,879 reviews)
Microwaves inside rooms

Reviewed on Jul 11, 2026

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
A city skyline with illuminated buildings, a river, and a bridge.

Irving Park

4 out of top 10 points of interest in this area
4/5(1 area review)

Irving Park is well-liked for its restaurants and live music. If you're hoping to get in some sightseeing, Milwaukee Avenue and COLOR CLUB are top spots, and you can jump on the metro at Irving Park Station (Blue Line) or Addison Station (Blue Line) to get around.

Find hotels in Irving Park

Find the Best Northwest Side Vacation Packages

Northwest Side Hotel Deals

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥24,883 per night from Jul 27 to Jul 28
￥24,883
￥29,585 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very Good! (1,735 reviews)
"Great location, clean, and a super breakfast!"

Reviewed on Jul 11, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
The price is ￥36,056 per night from Jul 26 to Jul 27
￥36,056
￥48,249 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (1,910 reviews)
"Staff was amazing, we had a single king bed corner suite with a separate room that has a pull out bed from the couch. It was a perfect setup for us because the kids had their own little room with their own tv and everything. The pullout couch bed was very uncomfortable, but we kinda figured it wouldn't ..."

Reviewed on Jul 12, 2026

Omni Chicago Hotel
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is ￥27,324 per night from Aug 3 to Aug 4
￥27,324
￥31,144 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (2,823 reviews)
"clean room"

Reviewed on Jul 12, 2026

Hyatt Regency O'Hare Chicago
See all 4,803 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.

Stay near popular Northwest Side attractions

Portage Park

After visiting Portage Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.
See properties

What to do in Northwest Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥4,389
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,992
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

￥6,502
per adult
92% of travellers recommend
Art Institute of Chicago
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 ￥295,012. 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.

Explore a world of travel with Expedia

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