Gross Point Holidays

    deals illustration

    Better together

    Save up to €185 when you book a flight and hotel together*
    stays illustration

    Find the right fit

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

    Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
21 Aug - 26 Aug
found 23 hours ago
Return flight included
Warsaw (WAW) to Chicago (ORD)
8.8/10 Excellent! (1,796 reviews)
The stay was good only thing i would say was a disappointment was the bathroom was small and it wasn’t a pool but our stay was great

Reviewed on 8 Jul 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
21 Aug - 26 Aug
found 23 hours ago
Return flight included
Warsaw (WAW) to Chicago (ORD)
9.2/10 Wonderful! (1,769 reviews)
Been there a couple times always a nice stay, great location

Reviewed on 8 Jul 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
21 Aug - 26 Aug
found 23 hours ago
Return flight included
Warsaw (WAW) to Chicago (ORD)
9/10 Wonderful! (627 reviews)
This place was secure and beautiful. The amenities were top notch & I felt 100% safe while there. Will return!

Reviewed on 7 Jul 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
21 Aug - 26 Aug
found 23 hours ago
Return flight included
Warsaw (WAW) to Chicago (ORD)
9.2/10 Wonderful! (1,333 reviews)
Hotel staff and room were awesome..bed very comfortable. Coffee shop was great had great fast breakfast options. Had Miss Rickie's one day was really great food. Only complaint would be the rooftop bar evening clientele...did not feel comfortable and they were loud and raucous.

Reviewed on 8 Jul 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
per person
21 Aug - 26 Aug
found 23 hours ago
Return flight included
Warsaw (WAW) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
The location of the hotel is excellent. One block from the river walk and just next to the train station for several lines. Room was spacious and bed was comfortable. Restaurant and Roof bar were both great. Staff friendly and helpful. We will definitely reccomend this hotel to friends and family.

Reviewed on 7 Jul 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

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

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
The price is €178 per night from 4 Aug to 5 Aug
€178
4 Aug - 5 Aug
includes taxes & fees
7.8/10 Good! (8,915 reviews)
"Well located for walking to Union Station, museums, restaurants, and art institute. A little difficulty getting past fences set up for Nascar event. Room temperature control (air conditioning) was on/off with no temperature control."

Reviewed on 8 Jul 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is €235 per night from 7 Aug to 8 Aug
€235
7 Aug - 8 Aug
includes taxes & fees
9/10 Wonderful! (2,000 reviews)
"Excellent hotel, walk distance from best spots at Chicago"

Reviewed on 8 Jul 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
The price is €178 per night from 6 Aug to 7 Aug
€178
6 Aug - 7 Aug
includes taxes & fees
8.8/10 Excellent! (2,409 reviews)
"I plan to make this hotel my home away from home in Chicago."

Reviewed on 9 Jul 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,255 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 €791. 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 featuring central business district, a city and a sporting event

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(125 reviews)

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

Navy Pier
Magnificent Mile - River North showing street scenes, signage and night scenes

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

River tour boat in Chicago

Architecture River Tour

€41
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

€38
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

€38
per adult
92% of travellers recommend
Chicago By Night River & 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.