
Central Chicago Beach Vacations
Book a Beach Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to ¥45,448 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top Beach vacation packages in Central Chicago
Price found within the past 48 hours. Click for updated prices.

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ¥103,798, price is now ¥70,950 per person
¥70,950
per person
Nov 22 - Nov 27
found 1 day ago
Roundtrip flight included
Memphis (MEM) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel
Reviewed on Oct 20, 2025

The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was ¥154,883, price is now ¥97,222 per person
¥97,222
per person
Nov 22 - Nov 27
found 1 day ago
Roundtrip flight included
Memphis (MEM) to Chicago (ORD)
9.2/10 Wonderful! (1,248 reviews)
We really like The Emily Hotel Chicago. We've stayed a few times this year because the location is very near many great restaurants and bars. The hotel itself has really good dining and lounge options. The staff treats us very well and the rooms and beds are clean and comfortable. A great hotel in a really fun part of town!
Reviewed on Oct 22, 2025

Arlo Chicago
Downtown Chicago
Save 100% on your flight
Price was ¥122,138, price is now ¥77,711 per person
¥77,711
per person
Nov 22 - Nov 27
found 1 day ago
Roundtrip flight included
Memphis (MEM) to Chicago (ORD)
9.2/10 Wonderful! (1,852 reviews)
We had an amazing time staying at the Arlo. The staff was very friendly, the check-in/check-out process was very fast. The room was always clean. The location of the hotel is extremely convenient. Everything was awesome. I’m 100% coming back when I’m in Chicago again.
Reviewed on Oct 22, 2025

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was ¥124,428, price is now ¥88,568 per person
¥88,568
per person
Nov 22 - Nov 27
found 1 day ago
Roundtrip flight included
Memphis (MEM) to Chicago (ORD)
9.4/10 Exceptional! (3,374 reviews)
This hotel was nearly perfect! Great staff. Great location. Clean. My only complaint was the ice machine was broken on our floor. We reported it to staff 3 separate occasions and it wasn’t fixed in the 5 days we were there. Hotel is located on a busy street so there is some noise but if that Doesn't bother you… this is perfect. Very walkable location! The staff there are fantastic. From the moment you walk in until the moment you leave. They understand the assignment. Highly recommend.
Reviewed on Oct 21, 2025

Hilton Chicago
Downtown Chicago
Price was ¥105,332, price is now ¥75,812 per person
¥75,812
per person
Nov 22 - Nov 27
found 1 day ago
Roundtrip flight included
Memphis (MEM) to Chicago (ORD)
8.4/10 Very Good! (2,261 reviews)
Location is really great but building needs a lot of updating. Didn’t get the room serviced the whole 3 nights but perhaps we had to call for them to do it. I had picked a room facing out and they changed it to one facing a wall. We didn’t bother complaining since we spent most of the time exploring the city. Breakfast buffet was very expensive but not really worth it.
Reviewed on Oct 22, 2025
Don't see what you're looking for?
See all available trips from Memphis to Central Chicago
View all trips5* Beach vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.


Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥307,410, price is now ¥251,867 per person
¥251,867
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The kitchen was VERY clean and very well stocked. Our room was as nice as any room as I have ever stayed in. The Hotel Manager and Pablo, the Director of Rooms, were outstanding!!! they were truly a credit to the Trump brand. I have stayed at the Trump International and would stay there again in a heartbeat.
Reviewed on Oct 20, 2025
Don't see what you're looking for?
See all available trips from Memphis to Central Chicago
View all trips4 Night Beach vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.


Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥307,410, price is now ¥251,867 per person
¥251,867
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The kitchen was VERY clean and very well stocked. Our room was as nice as any room as I have ever stayed in. The Hotel Manager and Pablo, the Director of Rooms, were outstanding!!! they were truly a credit to the Trump brand. I have stayed at the Trump International and would stay there again in a heartbeat.
Reviewed on Oct 20, 2025

Pendry Chicago
Downtown Chicago
Price was ¥249,900, price is now ¥218,036 per person
¥218,036
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.
Reviewed on Oct 16, 2025
Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.