Gross Point Vacations from ￥303,878

Book a Hotel + Flight or Car together to unlock savings

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    Save up to ￥45,448 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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The Latest Gross Point 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
Aug 6 - Aug 9
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,763 reviews)
Friendly bartender made the whole trip amazing, the beds and bathroom were really nice!

Reviewed on Jun 22, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
Aug 6 - Aug 9
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Amazing service!! Beautiful hotel!

Reviewed on Jun 22, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Aug 6 - Aug 9
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
Beautiful property. Amazing customer service.

Reviewed on Jun 17, 2025

The Hoxton Chicago

The Hoxton Chicago

4 out of 5
Downtown Chicago
per person
Aug 6 - Aug 9
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (1,000 reviews)
Overpriced. Small room. Terrible shower. Awful coffee in the room. No room cleaning or water replenish unless requested. Kind of like the laziest and most minimal service with a tiny space for a premium price. The servers in the restaurant Cira were almost rude, and support staff looked miserable. The rooftop pool is tiny, and has barely a dozen spots to sit. The hotel doesn't tell you that at night it turns into a nightclub! Good luck getting to your elevator, and then plan on waiting. Don't even try getting a drink at the bar. There must have been 200 people in the lobby. The only positive feedback is that the sound from the party doesn't travel to the 6th floor.

Reviewed on Jun 23, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Aug 6 - Aug 9
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (320 reviews)
I had no idea how nice this property would be! I had a full one-bedroom apartment and amazing view and amenities. 10/10, would stay again!

Reviewed on Jun 1, 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

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
The price is ￥22,346 per night from Jul 1 to Jul 2
￥22,346
￥26,233 total
Jul 1 - Jul 2
includes taxes & fees
8.4/10 Very Good! (4,261 reviews)
"Yes"

Reviewed on Jun 24, 2025

Embassy Suites by Hilton Chicago Downtown River North
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 ￥22,719 per night from Jul 1 to Jul 2
￥22,719
￥31,307 total
Jul 1 - Jul 2
includes taxes & fees
9/10 Wonderful! (1,919 reviews)
"Our favorite Chicago hotel. The location is perfect for exploring the city, dining, and walking. My only complaint is that the condition of the pool was not nearly as clean and clear as usual."

Reviewed on Jun 24, 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 ￥19,589 per night from Jul 6 to Jul 7
￥19,589
￥22,995 total
Jul 6 - Jul 7
includes taxes & fees
8.8/10 Excellent! (2,328 reviews)
"I loved the view from my room. Everything was great except the parking situation. 80 to 90$ a day to park so add that into your stay if you’re on a budget like me. Nice big tv’s."

Reviewed on Jun 22, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,233 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 ￥303,878. 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

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

Things to do

River tour boat in Chicago

Architecture River Tour

￥7,052
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥6,507
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

￥6,507
per adult
92% 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.