Gross Point Vacation Packages

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Your Gross Point Vacation

Enjoy amazing adventures when you book a Gross Point vacation package. Whether you're a history buff, foodie or just a traveler who loves to experience new places, there's something for everyone in this exciting city. Every good trip to Gross Point has to include a bit of sightseeing. What to check out first? Bahai House of Worship and Langdon Park Beach are key attractions. Whatever your travel plans or the size of your budget, organizing your ultimate tailored Gross Point vacation is a piece of cake with Expedia.

Top Holiday Package Deals in Gross Point

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,024, price is now CA $712 per person
CA $712
per person
Mar 31 - Apr 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.

Reviewed on Feb 16, 2026

La Banque Hotel

La Banque Hotel

4 out of 5
Price was CA $1,406, price is now CA $853 per person
CA $853
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.

Reviewed on Jan 26, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $2,539, price is now CA $1,599 per person
CA $1,599
per person
May 3 - May 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Clean amenities, amazing food, and great service!

Reviewed on Feb 27, 2026

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $2,526, price is now CA $1,815 per person
CA $1,815
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
The staff were lovely. As it was our anniversary, we were given a beautiful room overlooking the water tower and the lake. The room was exceptional - the bath tub, huge! The hotel itself was within walking distance to almost everywhere - the lake, the river, the magnificent mile. There were cafes and restaurants very close by. We had a fantastic time in Chicago because of this!

Reviewed on Feb 20, 2026

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was CA $2,238, price is now CA $1,618 per person
CA $1,618
per person
May 3 - May 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,002 reviews)
This was a trendy aesthetic hotel. It is in a great location. Had a good time.

Reviewed on Feb 26, 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 showing a city

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.

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 CA $132 per night from Mar 1 to Mar 2
CA $132
CA $155 total
Mar 1 - Mar 2
includes taxes & fees
8/10 Very Good! (9,893 reviews)
We mainly go to Chicago for medical appointments and it is *so awesome* that you can actually open the windows here.That is the main reason we chose it. Because Dad has cancer we aired it out and then ran our own air purifier. No bad smells or anything, we're just being cautious because of his health. ...

Reviewed on Feb 27, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from Mar 4 to Mar 5
CA $155
CA $220 total
Mar 4 - Mar 5
includes taxes & fees
9.4/10 Exceptional! (3,422 reviews)
This is our new go-to in the city. Great location, very comfortable beds. Pillows are unusually small, but they brought more quickly. Large bathroom with double sinks. Breakfast buffet was excellent and plentiful. Shout out to Frank during our very late check-in. Very friendly, funny and was quick ...

Reviewed on Feb 27, 2026

Hotel Riu Plaza Chicago
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 CA $154 per night from Mar 2 to Mar 3
CA $154
CA $181 total
Mar 2 - Mar 3
includes taxes & fees
8.6/10 Excellent! (5,692 reviews)
Hotel is beautiful and located in the heart of everything. Starbucks outside is a plus. Breakfast is excellent and rooms are spacious. Wish they have a whirlpool

Reviewed on Feb 27, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,558 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Gross Point vacation package cost?
From as low as CA $712. 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 central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

4.5/5(19 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
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(459 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $55
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $47
per adult
96% of travellers recommend
Color Factory Chicago Ticket
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.