Far North Side Vacations from ￥248,500

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The Latest Far North Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was ￥343,557, price is now ￥248,500 per person
￥248,500
per person
Nov 13 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (1,962 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.

Reviewed on Aug 25, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥353,710, price is now ￥268,396 per person
￥268,396
per person
Nov 13 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,316 reviews)
Staffs were super friendly and helpful. Buffet breakfast was great, location was near everything……

Reviewed on Aug 28, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was ￥358,844, price is now ￥278,143 per person
￥278,143
per person
Nov 13 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Very nice hotel and staff were pleasant. The area is okay but if you go a block over it is nicer. The river walk is very close and inviting.

Reviewed on Aug 25, 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was ￥323,910, price is now ￥251,450 per person
￥251,450
per person
Nov 13 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Great location and room was fantastic! Only negatives were a lengthy check in and access to the outside deck was closed at 10 PM. Probably a good idea for that, but it would’ve been nice to go out there for a nightcap.

Reviewed on Aug 26, 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was ￥409,499, price is now ￥319,112 per person
￥319,112
per person
Nov 13 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,099 reviews)
The Hotel is very convenient, but needs updating. The bathrooms are old, etc. The staff was very friendly and the dining options are excellent and very convenient given you’re in the middle of the airport.

Reviewed on Aug 26, 2025

Where to stay in Far North Side

Find the best Far North Side areas and neighborhoods for the activities you enjoy most. Learn more about Far North Side
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Rogers Park

1 out of top 10 points of interest in this area
4.5/5(80 area reviews)

Noted for its beaches and restaurants, there's plenty to explore in Rogers Park. Top attractions like Lake Michigan and North Shore Beach Park are major draws, and you can hop on the metro at Morse Station or Jarvis Station to see more of the city.

Find hotels in Rogers Park

Find the Best Far North Side Vacation Packages

Far North Side Hotel Deals

Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥22,400 per night from Sep 20 to Sep 21
￥22,400
￥26,296 total
Sep 20 - Sep 21
includes taxes & fees
8.4/10 Very Good! (1,130 reviews)
"It was very nice!!!!"

Reviewed on Aug 25, 2025

Marriott Chicago O'Hare
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥22,238 per night from Sep 1 to Sep 2
￥22,238
￥26,106 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (1,220 reviews)
Room clean and modern
"It was great and I appreciated the friendly staff and the cleanliness of my room. It was also very modern and just felt up to date."

Reviewed on Aug 25, 2025

The Wade
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 ￥19,795 per night from Sep 1 to Sep 2
￥19,795
￥23,236 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (9,016 reviews)
"I really enjoyed my stay here . The hotel is very historical and is known for hosting beautiful weddings, it’s huge , restaurants on property, and is very close to everything there is to see in downtown Chicago . Very close to the river walk , millennium park, coffee shops/breakfast, the loop , Taco ..."

Reviewed on Aug 25, 2025

Congress Plaza Hotel
See all 5,251 properties in Far North 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 Far North Side

Wrigley Field featuring cbd, a sporting event and a city

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 night scenes, a city and signage

Michigan Avenue

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
Navy Pier featuring a sunset and rides

Navy Pier

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

Navy Pier

What to do in Far North Side

River tour boat in Chicago

Architecture River Tour

￥6,127
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

￥6,651
per adult
96% 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

￥5,986
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Far North Side

Frequently asked questions

How much does a Far North Side vacation package cost?
Tailor make your Far North Side vacation package from only ￥248,500. Pick from any combination of rental cars, flights and hotels to build the getaway you've been dreaming about. Don't forget to add on a few experiences or tours!
How do I get a cheap travel package to Far North Side?
One of the simplest ways to save cash (and time) is to bundle your bookings with Expedia. Hotels, rental cars, flights and activities — we've got them all. Pick a combination that suits you and see your savings stack up. Of course, a travel package is never a one-size-fits-all. That's why we offer more than 550 air carriers and 1,000,000 properties throughout the world, which lets you customize your Far North Side getaway.
How far in advance should I book my Far North Side vacation?
It can be tricky to know when the best time is to book your Far North Side vacation. But usually the earlier you book, the cheaper the prices. In some cases, you can reserve your flights and hotels up to a year prior to departure. If you're thinking of a last-minute getaway, no need to stress! There are fantastic bargains announced on Expedia every day.
What does an Expedia Far North Side travel package include?
From flights and hotels to car rentals, Expedia can help you put together a Far North Side package that's perfect for you. Vacationing for a few weeks? Check out a rental car, hotel and flight bundle. If your break is short, a hotel and airfare deal could be more your style. Experiences can also be added after you've booked. Our travel packages make it simple to plan and save.
What should I know before booking a Far North Side travel package?
Our prices are always low. However, you'll enjoy even more bargains if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and lots of choice.
Can I choose my airline with a Far North Side Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines throughout the world. Our vacation packages give you the freedom to take your pick of available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Far North Side vacation package?
Your situation can change unexpectedly, so yes. You may be able to change or cancel your Far North Side vacation package for free within 24 hours of booking. For bookings made more than 24 hours ago, you can still cancel or make changes, but your car rental company, hotel or airline may charge a fee. Want more information? Take a look at our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.