Near North Side Vacations from ￥313,997

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The Latest Near North Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago Schaumburg

DoubleTree by Hilton Chicago Schaumburg

4 out of 5
Price was ￥373,915, price is now ￥313,997 per person
￥313,997
per person
Feb 20 - Feb 23
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
7.2/10 Good! (1,003 reviews)
The room was clean. Staff and bar was really nice.

Reviewed on Dec 18, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥471,930, price is now ￥365,182 per person
￥365,182
per person
Feb 20 - Feb 23
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!

Reviewed on Jan 3, 2026

Chicago Marriott Suites O'Hare

Chicago Marriott Suites O'Hare

4 out of 5
Price was ￥384,612, price is now ￥321,928 per person
￥321,928
per person
Feb 20 - Feb 23
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.8/10 Excellent! (1,002 reviews)
The staff were friendly and professional. The room was clean and as expected. Only drawback was the lack of amenities. Coffee was out of a machine in lobby and cost $4 - WiFi was not free and $15 a day.

Reviewed on Dec 28, 2025

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Downtown Chicago
Price was ￥394,990, price is now ￥331,453 per person
￥331,453
per person
Feb 20 - Feb 23
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (2,558 reviews)
Pool area is amazing.

Reviewed on Jan 8, 2026

Sonesta Chicago O'Hare Airport Rosemont

Sonesta Chicago O'Hare Airport Rosemont

3 out of 5
Price was ￥379,972, price is now ￥319,051 per person
￥319,051
per person
Feb 20 - Feb 23
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.6/10 Excellent! (1,633 reviews)
Very quiet considering proximity to the airport

Reviewed on Jan 7, 2026

Where to stay in Near North Side

Find the best Near North Side areas and neighborhoods for the activities you enjoy most. Learn more about Near North Side
Downtown Chicago showing a city

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Near North Side Hotel Deals

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 ￥13,998 per night from Jan 25 to Jan 26
￥13,998
￥16,432 total
Jan 25 - Jan 26
includes taxes & fees
8.8/10 Excellent! (3,660 reviews)
We had a wonderful stay at the Hilton. The staff was exceptionally helpful in providing any information we neede. A shout out to Latis and Christian, who were extremely friendly, always created us with a smile and we’re eager to help. We will definitely stay here again.

Reviewed on Jan 6, 2026

Hilton Chicago/Magnificent Mile Suites
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 ￥14,648 per night from Jan 19 to Jan 20
￥14,648
￥17,196 total
Jan 19 - Jan 20
includes taxes & fees
8.4/10 Very Good! (5,522 reviews)
Had a great stay.

Reviewed on Jan 8, 2026

Embassy Suites by Hilton Chicago Downtown River North
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥13,531 per night from Feb 8 to Feb 9
￥13,531
￥15,884 total
Feb 8 - Feb 9
includes taxes & fees
8.8/10 Excellent! (3,167 reviews)
The view stood out the most to me and the room was very clean and stayed clean. Me and my partner really enjoyed our stay!

Reviewed on Jan 7, 2026

Eurostars Magnificent Mile
See all 1,073 properties in Near 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.

Frequently asked questions

How much does a Near North Side vacation package cost?
Starting from only ￥313,997, a package is your passport to low-cost travel. Put together your Near North Side trip by picking from our wide range of hotels, airfares and rental cars.
How do I get a cheap travel package to Near North Side?
Secure flights that fit in with your schedule, add a hotel to your booking and watch the savings rack up with a Near North Side vacation package. It's that simple! From hotels and flights to rental cars and tours, Expedia makes traveling cheaply a cinch. And with more than 550 partner airlines and 1,000,000 properties throughout the world to choose from, you'll never be short of choice.
Where should I stay in Near North Side?
Vacationers come from all over to see McCormick Place and Millennium Park in Near North Side. Book a room near these awesome attractions and visit them whenever you please.
What are the top hotels in Near North Side?
Sable at Navy Pier Chicago, Curio Collection by Hilton and Kasa River North Chicago are a couple of the most well-known properties in Near North Side. Why not take a look at the facilities and rates at each and then decide?
How far in advance should I book my Near North Side vacation?
Travelers can normally compare international flights on Expedia within 12 months of departure. Booking late? With a stroke of luck, it's still possible to score a cheaper ticket only weeks before your journey.
What does an Expedia Near North Side travel package include?
Travel packages include hotels, rental cars and flights, but you can mix and match them to create your perfect Near North Side vacation. You can also add on a few activities and tours once you've made your booking. You're in control! When you combine your bookings with Expedia, you'll score deals you won't find elsewhere.
What should I know before booking a Near North Side travel package?
Whether it's relaxation or adventure you're seeking, a Near North Side vacation package lets you organize your escape your way. Plus, you'll get access to great discounts when you combine your accommodations with your flights and rental car. The more you bundle, the bigger the savings!
Can I choose my airline with a Near North Side Expedia vacation package?
Expedia offers access to more than 550 airline partners worldwide, so you sure can! Simply pick the carrier you want and create your ideal Near North Side vacation.
If I'm not able to travel, can I cancel my Near North Side vacation package?
Yes, you can. We get that even the best-laid plans can go awry, so we're here to help if you need to make changes to your Near North Side vacation package. You may be able to cancel or amend your itinerary for free if you've booked in the last 24 hours. Your airline, hotel or car rental company may charge you a fee if you booked more than 24 hours ago. Have a look at our Customer Service Portal for more information. Also, be sure to check your itinerary for the nitty-gritty on change fees.

Discover the most popular places to visit in Near North Side

Merchandise Mart

Merchandise Mart

You can learn about the history of Chicago with a trip to Merchandise Mart. Amble around this vibrant area's riverfront or experience its acclaimed art scene.

Merchandise Mart
Water Tower Place

Water Tower Place

Enjoy endless shopping, see exhibits of sporting memorabilia and attend shows at a live theater at this huge shopping mall.

Water Tower Place
John Hancock Center featuring a city, night scenes and landscape views

875 North Michigan Avenue

You can find out about the history of Chicago with a visit to 875 North Michigan Avenue. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

875 North Michigan Avenue

Things to do

Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

￥6,889
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,845
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

￥6,263
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.