Gross Point Holidays

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    Save up to S$134 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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

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

Top hotels in Gross Point

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 S$164 per night from 16 Apr to 17 Apr
S$164
16 Apr - 17 Apr
includes taxes & fees
8/10 Very Good! (10,041 reviews)
Property is always well maintained, very clean and tidy

Reviewed on 6 Apr, 2026

Congress Plaza Hotel
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 S$207 per night from 12 Apr to 13 Apr
S$207
12 Apr - 13 Apr
includes taxes & fees
9/10 Wonderful! (4,067 reviews)
The hotel is perfect. The view was beautiful. Room was clean, staff were professional and friendly. The food and drinks was amazing 😋 😍

Reviewed on 6 Apr, 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 S$235 per night from 19 Apr to 20 Apr
S$235
19 Apr - 20 Apr
includes taxes & fees
8.6/10 Excellent! (5,825 reviews)
The room was very clean but the amenities are quite dirty. In general is a big hotel with a lot of movement, many families and a lot of people everywhere, so the breakfast (which is great by the way) is very busy.

Reviewed on 6 Apr, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,549 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 holiday package cost?
From as low as . Yes, you read that right. Our Gross Point holiday packages are an awesome way to make your budget last longer. Bundle your favourite 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 holiday package. It's as easy as that! From flights and hotels to rental cars and activities, Expedia makes travelling 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 holiday?
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 holiday 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 travelling style.
If I'm not able to travel, can I cancel my Gross Point holiday package?
We totally get it — life doesn't always go according to plan. If you've booked a Gross Point holiday 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.

Popular places to visit

Wrigley Field

Wrigley Field

4.5/5(40 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

5/5(1 review)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

S$35
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

S$51
per adult
94% of travellers recommend
Art Institute of Chicago
Flyover in Chicago

Flyover in Chicago

S$49
per adult
98% of travellers recommend
Flyover in 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.