Gross Point Vacations from ￥223,048

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The Latest Gross Point Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥263,537, price is now ￥223,048 per person
￥223,048
per person
Nov 28 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Breakfast buffet was excellent. Shortage of cleaning staff created some problems—two times the room wasn’t serviced until after 5:00 p.m. Room was fine but we needed information about turning on and using the TV. Also needed instructions on using the soap dispensers in the bathroom. Seems trivial, but it’s the little things that separate good from excellent. Staff was cordial and helpful.

Reviewed on Sep 27, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥420,412, price is now ￥337,166 per person
￥337,166
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
It’s was very clean and safe

Reviewed on Sep 27, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was ￥280,959, price is now ￥226,887 per person
￥226,887
per person
Dec 3 - Dec 8
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (698 reviews)
Close to any and everything u wanna do highly suggested place to stay

Reviewed on Sep 19, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was ￥281,081, price is now ￥232,163 per person
￥232,163
per person
Dec 3 - Dec 8
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,826 reviews)
Great room. Very nice staff. We loved it. The scent in the lobby was nice but a little strong. I would stay here again.

Reviewed on Sep 27, 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was ￥433,574, price is now ￥369,947 per person
￥369,947
per person
Nov 1 - Nov 7
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,123 reviews)
We were dead tired from a long flight from Turkey the day before. We slept well most of the night but still did not want to drag our heavy bags to Terminal 5 via the light rail. The hotel graciously transported us directly to the outdoor check in and we were on our way to security an hour ahead of our schedule! Thanks. The only improvement would be to service the slightly noisy air conditioner in our room.

Reviewed on Sep 20, 2025

Where to stay in Gross Point

Find the best Gross Point areas and neighborhoods for the activities you enjoy most. Learn more about Gross Point
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

Gross Point 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 ￥20,081 per night from Oct 26 to Oct 27
￥20,081
￥23,573 total
Oct 26 - Oct 27
includes taxes & fees
7.8/10 Good! (9,307 reviews)
"Parking situation is ridicules, hallways carpet very filthy. I understand it’s an older hotel but needs to be kept up. Bathroom door didn’t even close."

Reviewed on Sep 25, 2025

Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥15,969 per night from Oct 28 to Oct 29
￥15,969
￥21,378 total
Oct 28 - Oct 29
includes taxes & fees
7.8/10 Good! (2,387 reviews)
"It felt cozy and comfortable. The room was a little bit dusty and the night light was not working."

Reviewed on Sep 24, 2025

Freehand Chicago
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 ￥24,016 per night from Oct 20 to Oct 21
￥24,016
￥28,194 total
Oct 20 - Oct 21
includes taxes & fees
8.8/10 Excellent! (2,946 reviews)
"This hotel was clean and the staff was very helpful and friendly. Parking is expensive, but that’s the case everywhere in Chicago. The view of the lake and surrounding buildings is very nice! The location is excellent and easy walking distance to everything you want to do in Chicago."

Reviewed on Sep 24, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,266 properties in Gross Point
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 Gross Point vacation package cost?
From as low as ￥223,048. Yes, you read that right. Our Gross Point vacation packages are an awesome way to make your budget last longer. Bundle your favorite hotels, flights and rental car and get out and see this vibrant destination.
How do I get a cheap travel package to Gross Point?
Search for flights that suit your schedule, add a hotel to your booking and watch the savings stack up with a Gross Point vacation package. It's as easy as that! From flights and hotels to rental cars and activities, Expedia makes traveling on the cheap easy. And with more than 550 partner airlines and 1,000,000 properties around the world to select from, you won't be short of choice.
Where should I stay in Gross Point?
Stay where the action happens. Many people book hotels in the vicinity of popular attractions, like Bahai House of Worship, Langdon Park Beach and Wilmette Park District Swimming Beach.
How far in advance should I book my Gross Point vacation?
While prices change from time to time, we generally recommend booking your spot as soon as possible. Most international fares can be compared on Expedia up to a year in advance. If circumstances have left you booking late, you might still be lucky. Cheaper tickets to Gross Point sometimes occur only weeks before departure.
What does an Expedia Gross Point travel package include?
With Expedia, you can select any combination of hotels, car rentals and flights to build your perfect Gross Point travel package. Once you've made your booking, you can add on fun stuff like activities and tours. Don't forget — the more you bundle, the more you stand to save!
What should I know before booking a Gross Point travel package?
When you book your flights, hotels and car rentals together, you'll nab terrific discounts. Whether you're planning a rural escape in a cottage or would rather stay in a ritzy city hotel, Expedia can make it happen for less.
Can I choose my airline with a Gross Point Expedia vacation package?
Yes, of course. We offer more than 550 partner airlines around the world, so go with the carrier that's a good fit for your budget and traveling style.
If I'm not able to travel, can I cancel my Gross Point vacation package?
We totally get it — life doesn't always go according to plan. If you've booked a Gross Point vacation package and need to amend or cancel it, we're here to help. We recommend having a look at our Customer Service Portal first for information. But generally, if you've booked your package in the last 24 hours, you may be able to cancel or change your itinerary free of charge. If it's been longer than 24 hours, your airline, hotel or car rental company may impose a fee.

Discover the most popular places to visit in Gross Point

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

Things to do

River tour boat in Chicago

Architecture River Tour

￥7,144
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

￥6,633
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

￥6,633
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
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.