
Historic Route 66 Adults Only Holidays
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Top flight + Adults Only hotel deals in Historic Route 66
Price found within the past 48 hours. Click for updated prices.

Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was £1,514, price is now £1,124 per person
£1,124
per person
6 Jul - 12 Jul
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
8.4/10 Very Good! (1,954 reviews)
Excelente ubicación! La habitación muy cómoda! Lo recomiendo!
Reviewed on 1 Jun 2026

The Emily Hotel
Downtown Chicago
Price was £2,030, price is now £1,497 per person
£1,497
per person
28 Aug - 4 Sept
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (1,320 reviews)
Great gym. I like that there was a coffee shop downstairs as well. Room was very clean and comfortable.
Reviewed on 5 Jun 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was £1,965, price is now £1,469 per person
£1,469
per person
11 Jul - 18 Jul
found 23 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,519 reviews)
Loved the location. Fitness room was a little disappointing because it’s small and the there are only 2 peloton bikes, but one was out of commission.
Reviewed on 4 Jun 2026

Level Chicago – Old Town
Downtown Chicago
Price was £1,904, price is now £1,430 per person
£1,430
per person
12 Aug - 16 Aug
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9/10 Wonderful! (481 reviews)
Very clean and loved the location and amenities with the store on the first floor was fantastic
Reviewed on 3 Jun 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £2,676, price is now £2,033 per person
£2,033
per person
11 Jul - 18 Jul
found 22 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,886 reviews)
We love the pool, cleanliness in the room .Friendly staff
Reviewed on 6 Jun 2026
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Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £2,676, price is now £2,033 per person
£2,033
per person
11 Jul - 18 Jul
found 22 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,886 reviews)
We love the pool, cleanliness in the room .Friendly staff
Reviewed on 6 Jun 2026

Nobu Hotel Chicago
Downtown Chicago
Price was £2,739, price is now £2,264 per person
£2,264
per person
11 Jul - 18 Jul
found 22 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (854 reviews)
Beautiful room. Well appointed. love the ambiance. Ashley Cartagena was very helpful with reservations!! Great location. Do not eat here, food is not good especially for the price. Rooftop bar view is cute but cocktails not great, I would skip them. There are dozens of cute coffee shops, bakeries, restaurants, bars & shops all steps away. would definitely stay here again.
Reviewed on 28 May 2026

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View all trips3 Night Adults Only holidays in Historic Route 66
Price found within the past 48 hours. Click for updated prices.

The Talbott, Autograph Collection
Downtown Chicago
Price was £1,059, price is now £906 per person
£906
per person
30 Aug - 2 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (117 reviews)
We thoroughly enjoyed our stay. The location was excellent, conveniently close to everything we needed. The room was spacious and spotless. The breakfast was fantastic, offering a wide variety of options to choose from.
Reviewed on 17 May 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was £1,497, price is now £1,258 per person
£1,258
per person
30 Aug - 2 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,886 reviews)
We love the pool, cleanliness in the room .Friendly staff
Reviewed on 6 Jun 2026

Pendry Chicago
Downtown Chicago
Price was £1,223, price is now £1,033 per person
£1,033
per person
30 Aug - 2 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,121 reviews)
I absolutely loved it! I little bit noisy but close to literally everything!
Reviewed on 2 Jun 2026
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View all trips4 Night Adults Only holidays in Historic Route 66
Price found within the past 48 hours. Click for updated prices.

Level Chicago Fulton Market
Downtown Chicago
Price was £1,634, price is now £1,259 per person
£1,259
per person
12 Aug - 16 Aug
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (488 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.
Reviewed on 22 May 2026

Level Chicago – Old Town
Downtown Chicago
Price was £1,904, price is now £1,430 per person
£1,430
per person
12 Aug - 16 Aug
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9/10 Wonderful! (481 reviews)
Very clean and loved the location and amenities with the store on the first floor was fantastic
Reviewed on 3 Jun 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was £1,769, price is now £1,380 per person
£1,380
per person
12 Aug - 16 Aug
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (2,519 reviews)
Loved the location. Fitness room was a little disappointing because it’s small and the there are only 2 peloton bikes, but one was out of commission.
Reviewed on 4 Jun 2026
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* 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.










