Far Southwest Side Adults Only Holidays
Book a Adults Only Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £335 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Top flight + Adults Only hotel deals in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was £1,087, price is now £853 per person
£853
per person
3 Jun - 7 Jun
found 1 hour ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,573 reviews)
the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well.
The location is excellent and i would go back.
Reviewed on 4 Mar 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,554, price is now £1,020 per person
£1,020
per person
3 Jun - 7 Jun
found 1 hour ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Everything was great, except for the rooftop that was not open because which was the main reason we chose this hotel
Reviewed on 10 Mar 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was £1,815, price is now £1,305 per person
£1,305
per person
23 Apr - 29 Apr
found 1 hour ago
Return direct flight included
London (LGW) to Chicago (ORD)
8.6/10 Excellent! (2,070 reviews)
Very nice & clean hotel and near the Bean and shops are walkable.
Reviewed on 3 Mar 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
Price was £1,683, price is now £1,287 per person
£1,287
per person
23 Apr - 29 Apr
found 1 hour ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
This was my first time ever staying at the Kimpton and it was absolutely amazing
Reviewed on 8 Mar 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was £1,248, price is now £983 per person
£983
per person
23 Apr - 29 Apr
found 1 hour ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.2/10 Wonderful! (1,407 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on 9 Mar 2026
Don't see what you're looking for?
See all available trips from Dublin to Far Southwest Side
View all trips5* Adults Only holidays in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.
Waldorf Astoria Chicago
Downtown Chicago
Price was £1,843, price is now £1,480 per person
£1,480
per person
26 Apr - 30 Apr
just found
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Nice bellmen, nice front staff, rooms were cozy and well kept. Everyone was very friendly and helpful. We would stay again.
Reviewed on 1 Mar 2026
Park Hyatt Chicago
Downtown Chicago
Price was £1,552, price is now £1,380 per person
£1,380
per person
26 Apr - 30 Apr
just found
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,001 reviews)
The room was a little dated. I was surprised that you didn’t have CNBC as a TV choice, I thought the gym was dated and the WiFi was inadequate
Reviewed on 28 Feb 2026
Don't see what you're looking for?
See all available trips from Dublin to Far Southwest Side
View all trips3 Night Adults Only holidays in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was £981, price is now £804 per person
£804
per person
4 Jun - 7 Jun
found 1 hour ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,573 reviews)
the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well.
The location is excellent and i would go back.
Reviewed on 4 Mar 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was £1,329, price is now £924 per person
£924
per person
4 Jun - 7 Jun
found 1 hour ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Everything was great, except for the rooftop that was not open because which was the main reason we chose this hotel
Reviewed on 10 Mar 2026
The Emily Hotel
Downtown Chicago
Price was £1,166, price is now £969 per person
£969
per person
4 Jun - 7 Jun
found 1 hour ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,310 reviews)
Very cool, gorgeous hotel. The rooms offered a lot of amenities and had a fun industrial vibe. The bed was very comfortable, and we slept great! The staff was incredibly helpful. I would definitely stay at The Emily again.
Reviewed on 7 Mar 2026
Don't see what you're looking for?
See all available trips from Dublin to Far Southwest Side
View all trips4 Night Adults Only holidays in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was £1,087, price is now £853 per person
£853
per person
3 Jun - 7 Jun
found 1 hour ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.2/10 Very Good! (2,573 reviews)
the staff was very friendly and helpful in a number of areas. The coffee was good each morning and the food as well.
The location is excellent and i would go back.
Reviewed on 4 Mar 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was £1,554, price is now £1,020 per person
£1,020
per person
3 Jun - 7 Jun
found 1 hour ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,438 reviews)
Everything was great, except for the rooftop that was not open because which was the main reason we chose this hotel
Reviewed on 10 Mar 2026
The Emily Hotel
Downtown Chicago
Price was £1,384, price is now £1,093 per person
£1,093
per person
3 Jun - 7 Jun
found 1 hour ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,310 reviews)
Very cool, gorgeous hotel. The rooms offered a lot of amenities and had a fun industrial vibe. The bed was very comfortable, and we slept great! The staff was incredibly helpful. I would definitely stay at The Emily again.
Reviewed on 7 Mar 2026
Don't see what you're looking for?
See all available trips from Dublin to Far Southwest Side
View all tripsMore holidays you might like
* 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.
