Gross Point Holidays

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    Save up to £750 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

  • Rest easy

    Packages with flights are ATOL protected

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.
  • 2 restaurants; breakfast, lunch and dinner served
    Jul 30 - Aug 3

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (3,730 reviews)
    "We stayed in this hotel in our daughter's wedding weekend. It was wonderful, the river and city view from our 18th story room was spectacular. I recommend it to.all ages."
    Reviewed June 7, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £1,713
    £1,296
    per traveller
    found 1 day ago
    LondonHouse Chicago, Curio Collection by Hilton
  • Terrace/patio
    Jul 30 - Aug 3

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (2,534 reviews)
    "This is an amazing place. Everything you can think of all under 1 roof. My hotel view was amazing. I am looking forward to coming annually."
    Reviewed June 8, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £1,877
    £1,398
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Full-sized fridge, microwave, oven, stovetop
    Aug 20 - Aug 25

    Level Chicago – Old Town + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.0/10 - Wonderful (489 reviews)
    "Very clean and loved the location and amenities with the store on the first floor was fantastic"
    Reviewed June 3, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £1,964
    £1,495
    per traveller
    found 7 hours ago
    Level Chicago – Old Town
  • Dinner served
    Jul 30 - Aug 4

    Kimpton Gray Hotel by IHG + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (1,005 reviews)
    "Nice staff clean room would stay again."
    Reviewed June 6, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £2,062
    £1,606
    per traveller
    found 1 day ago
    Kimpton Gray Hotel by IHG
  • Breakfast and dinner served
    Jul 30 - Aug 3

    Omni Chicago Hotel + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.2/10 - Wonderful (1,797 reviews)
    "beautiful room city view excellent location quiet and comfortable"
    Reviewed June 9, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £1,701
    £1,330
    per traveller
    found 1 day ago
    Omni Chicago Hotel

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 £121 per night from 29 Jun to 30 Jun
£121
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (10,228 reviews)
"Housekeeping did not come a single time in the four days and four nights I stayed there. The beds were not made nor was the trash taken out a single time . I had to phone them twice to receive bath towels. I was using Uber eats take out bags as trash bags due to the lack of housekeeping not ..."

Reviewed on 9 Jun 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The price is £142 per night from 1 Jul to 2 Jul
£142
1 Jul - 2 Jul
includes taxes & fees
7.8/10 Good! (1,547 reviews)
"Everything perfect"

Reviewed on 9 Jun 2026

The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is £136 per night from 28 Jun to 29 Jun
£136
28 Jun - 29 Jun
includes taxes & fees
8.8/10 Excellent! (2,638 reviews)
"Upsetting that I was given a room that I had to haul all of my luggage up 16 steep stairs. No other room options. I had reserved a room months in advance. The front desk lady said a few stairs, which I found odd being that there is an elevator. Beware…the top floor is by stairs only! Front desk lady ..."

Reviewed on 9 Jun 2026

Hyatt Regency O'Hare Chicago
See all 4,451 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 . 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
Millennium Park

Millennium Park

4.5/5(147 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
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
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

£81
per adult
88% of travellers recommend
Chicago C3® by CityPASS®
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.