Gross Point Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Gross Point Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
$791
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Ontario Intl. Airport (ONT) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Great Accommodations for a quick weekend. The gym was topnotch.
Reviewed on Aug 25, 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
$871
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
I booked this facility bcos the beds were king size. Little did I realize that the beds took up all the space in the little rooms. Be mindful of the room space, if you need space this is not the place for you. Location was excellent. 2 blocks from Michigan ave and all the food amenities you can ask for. I would come here again but it would just be a few people (2) to a room.
Reviewed on Aug 25, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
$888
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Arlo Chicago
Downtown Chicago
$1,012
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Overall, I enjoyed my stay at Arlo Chicago. The staff were wonderful, especially Antoine, who went above and beyond helping us get settled and navigate Uber pickups. His customer service was exceptional!
The location is a HUGE plus. It’s extremely walkable and truly in the heart of downtown. Millennium Park and the Bean are about 3 minutes away, with Michigan Ave, the Riverwalk, Magnificent Mile, restaurants and shopping nearby. Garrett Popcorn is across the street, Sweetgreen downstairs and Starbucks and Wildberry Cafe is up the block.
Uber tip: Use 171 N. Garland Court for pickup. The hotel prefers rideshares in the rear to avoid congestion.
The hotel is modern and beautiful. Our room had a nice city view with a glimpse of Lake Michigan. Rooms are small and the walls are thin, so you can hear neighboring rooms.
My only concern was housekeeping. While I wouldn’t call the hotel dirty, the cleaning didn’t meet my personal standard. We found crumbs and a wrappers around the bed frame and residue from previous guests in the bathroom on the walls and in the shower. Daily housekeeping made the beds, but the floors didn’t appear to be thoroughly vacuumed.
Overall, I’d still recommend Arlo for the amazing location and staff. More attention to detail with housekeeping would make the experience even better!
Reviewed on Aug 25, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
$960
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Just wow,Just Perfect,Nice Room and Amazon staff
Reviewed on Aug 24, 2026
Sentral Michigan Avenue
Downtown Chicago
$976
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Book a stay at this business-friendly aparthotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.
Pool was closed both days I stayed
Reviewed on Aug 24, 2026
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View all tripsGross Point Vacation Packages
Trying to plan a way to package your Gross Point flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® Gross Point vacation packages can help. We can assist you with hotel bookings, flights, car rentals and more. You can get almost everything you need here to make your trip to Gross Point perfect. Our Travel Center is a one-stop shop where you can put together the best Gross Point vacation package for you. AARP Travel Center has an incredible selection of flights and hotels, as well as Gross Point endeavors to select from.
Hotels in Gross Point
With 4310 hotels and resorts in Gross Point to choose from, you will find one that is perfect for you.
We have great deals on everything from luxury hotels that satisfy all the vacation must-haves to affordable hotels perfect for those on looking to save. You can scan all the possibilities and pick the accommodation that is best for you. With AARP Travel Center's Gross Point hotel packages, you not only get a great rate on your flight, but also a terrific place to stay.
Things to do in Gross Point
People from all over make this city their vacation destination, and with good reason. A little curiosity and asking the right people, like your hotel's concierge, goes a long way into having a unique experience.
Looking for more? Then Check out AARP Travel Center's "Things to Do" Page.
Package Your Gross Point Vacation and Save
As an AARP Member, you get to benefit from all the great savings. You can save on select hotels worldwide, flights, and car rentals. No matter what Gross Point vacation package you pick, you can rest easy knowing that you already saved on your trip. The hardest packing you'll have to do is for your suitcase. Book now and get ready for your Gross Point vacation.
Top Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
Stay at this aparthotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 3 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
River Hotel
75 East Wacker Drive Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
Fairmont Chicago at Millennium Park
200 North Columbus Drive Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Hilton Chicago
720 S Michigan Ave Chicago IL
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
Holiday Inn Chicago Dwtn - The Mart by IHG
350 West Wolf Point Plaza, Building 2 Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Thu, Oct 15 - Mon, Oct 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$148
Roundtrip
found 2 days ago
Thu, Oct 15 - Mon, Oct 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$173
Roundtrip
found 2 days ago
Thu, Oct 15 - Mon, Oct 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$183
Roundtrip
found 2 days ago
Thu, Oct 1 - Sun, Oct 4
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197
Roundtrip
found 1 day ago
Thu, Oct 1 - Sun, Oct 4
LAX
Los Angeles Intl.
MDW
Midway Intl.
$197
Roundtrip
found 1 day ago
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