Gross Point Holidays from £1,165

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Your Gross Point Holiday

Enjoy amazing adventures when you book a Gross Point holiday package. Whether you're a history buff, foodie or just a traveller 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, organising your ultimate tailored Gross Point holiday is a piece of cake with Expedia.

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
9 Oct - 14 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,950 reviews)
Great hotel, very clean. They could add a bar in the lobby and one more elevator

Reviewed on 4 Aug 2025

L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
9 Oct - 14 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,747 reviews)
The staff were nice !!! Rooms were clean!!

Reviewed on 4 Aug 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
9 Oct - 14 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on 22 Jul 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
21 Sept - 25 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
Just a fantastic check-in, very classy hotel and went overboard decorating for my 19-year-old’s birthday and giving Little goodies!

Reviewed on 26 Jul 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
9 Oct - 14 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,049 reviews)
Amazing view, nice room sizes and very clean

Reviewed on 3 Aug 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 featuring 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

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 £118 per night from 5 Aug to 6 Aug
£118
5 Aug - 6 Aug
includes taxes & fees
7.8/10 Good! (8,938 reviews)
"Very convenient location. Easy check-in, even with a very crowded lobby. Polite staff."

Reviewed on 1 Aug 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £172 per night from 21 Aug to 22 Aug
£172
21 Aug - 22 Aug
includes taxes & fees
8.2/10 Very Good! (1,820 reviews)
"Beautiful gilded age feel. Long wait for elevators is my only complaint"

Reviewed on 3 Aug 2025

Palmer House a Hilton Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is £129 per night from 24 Aug to 25 Aug
£129
24 Aug - 25 Aug
includes taxes & fees
8.8/10 Excellent! (1,330 reviews)
"Nice location"

Reviewed on 1 Aug 2025

Crowne Plaza Chicago West Loop by IHG
See all 4,376 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 Holidays
All Inclusive Holidays
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Beach Holidays
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Family Friendly Holidays

Frequently asked questions

How much does a Gross Point travel package cost?
From as low as £1,165. Yes, you read that right. Our Gross Point packages are an awesome way to make your budget go further. Bundle your preferred hotels, flights and rental car and get out and explore this destination your way.
If I'm not able to travel, can I cancel my Gross Point travel package?
Don't worry if you're rethinking your Gross Point travel package — it's possible to change or amend your booking. And if you've booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your airline, hotel or car rental company. We understand your circumstances can suddenly change, so look up our Customer Service Portal if that occurs. When you're ready to make changes, we'll be here to help.
How do I get a cheap travel package to Gross Point?
You'll save a ton of money if you combine your flights, car rentals and hotels into a Gross Point travel package. Sometimes cheap packages mean fewer choices. But that's not the case with Expedia. We offer over 550 air carriers and 1,000,000 properties across the world, which means you'll always have plenty of variety to choose from. Like to save even more? Add some interesting activities to your package deal to unlock even bigger discounts! After all, travel is about more than simply getting to your destination.
Does Expedia offer Book Now, Pay Later Gross Point holidays?
Expedia has joined forces with online lender Klarna to make your next getaway easier on the purse strings. Paying by instalment means you can spread the costs of your next dream escape, leaving you with more cash to spend while you're away. Klarna has several payment plans to choose from, so you're sure to find something that fits your budget. Consider these flexible payment options:

  • Pay monthly holidays: Klarna offers convenient monthly payment plans that suit all types of budgets, so you can have that well-earned holiday sooner.
  • Pay in instalments holidays: If you want to pay off your getaway across multiple transactions, holidays paid in instalments might be the best option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: Clicking on the "book now" button is easier with this payment option. Put down a small deposit on your holiday and then start working on your travel plans.

Where should I stay in Gross Point?
Stay where the action is. Many visitors favor hotels around top sights, like Bahai House of Worship, Langdon Park Beach and Wilmette Park District Swimming Beach.
What are the top hotels in Gross Point?
Residence Inn by Marriott Chicago Wilmette/Skokie is one of Gross Point's most well-known properties. Reserve a room here and you can sleep soundly knowing you're in good hands.
How far in advance should I book my Gross Point holiday?
Search Expedia to compare international fares as soon as possible. In most cases, you can purchase a seat up to 12 months prior to departure. If it's too early for your preferred carrier, or you have to book last minute, don't despair. Low prices to Gross Point sometimes occur within weeks of the date of departure.
What does an Expedia Gross Point travel package include?
From airfares and hotels to car rentals, Expedia can help you put together a Gross Point package that fits you. Heading off for a few weeks? Check out a hotel, rental car and flight bundle. If your break is short, a hotel and airfare deal may be more your style. Tours and activities can be added after you've booked. Our travel packages make it a breeze to save and plan.
What should I know before booking a Gross Point travel package?
So many places to explore, so many things to see. With a package, you can cross more of them off your list. Bundle your hotels, flights and rental cars and enjoy big savings.
Can I choose my airline with a Gross Point Expedia travel package?
With a travel package, you're always in charge. Whether you're looking to fly to Gross Point in coach or first class, simply select from the available airline options. Expedia has access to more than 550 airline partners around the world.

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

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 which includes street scenes, signage and night scenes

Michigan Avenue

You can find the perfect gifts to bring home 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

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

£31
per adult
96% of travellers recommend
Architecture River Tour
Couple on a sightseeing boat in Chicago

Skyline Lake Tour

£22
per adult
92% of travellers recommend
Skyline Lake Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

£33
per adult
100% of travellers recommend
Chicago Sightseeing River and 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. Flight-inclusive packages are ATOL protected.