Gross Point Vacations from ￥279,254
Book a Hotel + Flight or Car together to unlock savings
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- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
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The Latest Gross Point Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥361,801
per person
Oct 18 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,957 reviews)
The hotel itself is nice! But I want to write a review about the STAFF! I have never stayed in a hotel where the staff is so well trained, professional, respectful, serving with positive attitude and smile, make you feel at home, spoil you and so much more! I absolutely wanted to stay longer because of the TOP NOTCH SERVICE! We need to give credits where credit is due and THIS is one of them!
Another positive point was our room had a kitchenette with stove, utensils, a FULL BAR WITH AFFORDABLE PRICES!!! The room service is open 24/7 and that’s something rare that a lot of hotels don’t have!
The bathtub was huge 🥰😍 Probablt my favorite amenities! Loved how the rooms were cleaned by the staff! We didn’t even have to ask! I have so many positive things to say! ABSOLUTELY RECOMMEND THIS HOTEL! You won’t regret it! ❤️❤️❤️
Reviewed on Aug 10, 2026
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
4 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.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Theatre District
While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).
Gross Point Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
￥16,655
￥19,801 total
Sep 8 - Sep 9
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
￥22,555
￥26,816 total
Aug 30 - Aug 31
includes taxes & fees
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
￥33,153
￥38,918 total
Aug 30 - Aug 31
includes taxes & fees
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 ￥279,254. 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.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
￥3,920
per adult
90% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
￥7,518
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.