Gross Point Holidays from £1,284

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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.
Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Downtown Evanston
Price was £1,668, price is now £1,284 per person
£1,284
per person
18 May - 25 May
found 17 hours ago
Return flight included
London (LON) to Chicago (ORD)
7.6/10 Good! (758 reviews)
Nice dinning spot, great service

Reviewed on 30 Mar 2026

The Chicago Hotel Collection - Wrigleyville

The Chicago Hotel Collection - Wrigleyville

3.5 out of 5
Lakeview
Price was £1,988, price is now £1,533 per person
£1,533
per person
28 Jun - 5 Jul
found 9 hours ago
Return flight included
London (LHR) to Chicago (ORD)
7/10 Good! (980 reviews)
We didn’t have a car. Walking to everything was easy. They need to work on hot water . Showers were like warm to cold.

Reviewed on 12 Apr 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £3,100, price is now £2,408 per person
£2,408
per person
5 Jun - 12 Jun
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!

Reviewed on 7 Apr 2026

The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

5 out of 5
Downtown Chicago
Price was £2,136, price is now £1,680 per person
£1,680
per person
28 Jun - 5 Jul
found 9 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
The hotel and service were emaculate

Reviewed on 11 Apr 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was £1,760, price is now £1,397 per person
£1,397
per person
28 May - 31 May
found 22 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (902 reviews)
Clean nice view enjoyed my stay

Reviewed on 10 Apr 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

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 £108 per night from 26 Apr to 27 Apr
£108
26 Apr - 27 Apr
includes taxes & fees
8/10 Very Good! (10,123 reviews)
It needs A LOT of maintenance.

Reviewed on 13 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 £104 per night from 26 Apr to 27 Apr
£104
26 Apr - 27 Apr
includes taxes & fees
9/10 Wonderful! (4,118 reviews)
Great room

Reviewed on 12 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 £121 per night from 26 Apr to 27 Apr
£121
26 Apr - 27 Apr
includes taxes & fees
8.6/10 Excellent! (5,848 reviews)
Great location, great staff, great rooms!

Reviewed on 12 Apr 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,529 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
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Gross Point travel package cost?
From as low as £1,284. 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

Wrigley Field

4.5/5(40 reviews)

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

Wrigley Field
Navy Pier

Navy Pier

4/5(127 reviews)

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

Navy Pier
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(14 reviews)

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

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Flyover in Chicago

Flyover in Chicago

£29
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. Flight-inclusive packages are ATOL protected.