
Chicago Luxury Holidays
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Price found within the past 48 hours. Click for updated prices.

Central Loop Hotel
Downtown Chicago
per person
21 Aug - 26 Aug
found 9 hours ago
Return flight included
Warsaw (WAW) to Chicago (ORD)
8.6/10 Excellent! (1,778 reviews)
It’s a terrific location and the room was clean and comfortable. It seemed the communication between the checkout staff and house keeping was really lacking, with an expectation that the latter try to figure out when guests had checked out, which made my checkout day very awkward. I’d recommend the hotel if you’re visiting Chicago, but my checkout experience could have been much better.
Reviewed on 7 Jul 2025

The Royal Sonesta Chicago River North
Downtown Chicago
per person
21 Aug - 25 Aug
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,822 reviews)
There are actually 2 of these, except one is located downtown in the middle of all the nightlife. Stay was nice, hotel was clean, staff was great.
Reviewed on 8 Jul 2025

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
per person
21 Aug - 25 Aug
found 1 day ago
Return flight included
Dublin (DUB) 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

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
per person
21 Aug - 25 Aug
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,353 reviews)
Professional service. Room service came daily to clean which was very nice. Quality shampoo/conditioner/wash. Great view. Would have liked a microwave, but mini fridge was nice.
Reviewed on 8 Jul 2025

L7 Chicago by LOTTE
Downtown Chicago
per person
21 Aug - 25 Aug
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (2,549 reviews)
This hotel was in an ideal part of the city. Walkable to most popular attractions and restaurants. The rooms are updated and furnished nicely. We got a river view room and enjoyed the oversized window nook. Lastly, it was my husband's birthday and room service left some cute and tasty tiny cakes for us to enjoy.
The only thing that I feel they could improve on is the drawer space. There were only 2 small drawers to put clothes in (aside from the closet). Above the drawers was an area to unpack your suitcase, so I just left my suitcase there an picked my clothes from there, my husband used the suitcase folding rack to hold his clothing. This was not a big deal because the room was spacious and I didn't feel like the suitcases out like that made the room look messy.
Lastly, Expedia kinda dropped the ball with sending me a notification the day before check-in stating:
"Your itinerary is ready. Ask for your VIP Access perk at check-in to L7 Chicago by LOTTE 👑"
At check in the person working the front desk had no idea what I was referring to, so I showed them the notification and they responded by saying something along the lines that because this hotel is somewhat new and is owned by a Korean company, that they probably offer that perk at their other hotels, but just not at this one yet. I just felt a little foolish, so just FYI Expedia bookers!
Reviewed on 8 Jul 2025
Price found within the past 48 hours. Click for updated prices.

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
per person
21 Aug - 25 Aug
found 1 day ago
Return flight included
Dublin (DUB) 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

The Royal Sonesta Chicago River North
Downtown Chicago
per person
21 Aug - 25 Aug
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,822 reviews)
There are actually 2 of these, except one is located downtown in the middle of all the nightlife. Stay was nice, hotel was clean, staff was great.
Reviewed on 8 Jul 2025

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
per person
21 Aug - 25 Aug
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,353 reviews)
Professional service. Room service came daily to clean which was very nice. Quality shampoo/conditioner/wash. Great view. Would have liked a microwave, but mini fridge was nice.
Reviewed on 8 Jul 2025

Trump International Hotel & Tower Chicago
401 N Wabash Ave, Chicago, IL
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,632 reviews)
"From the moment we arrived, this hotel exceeded every expectation. The staff greeted us warmly and went out of their way to make us feel welcome. Check-in was seamless, and our room was ready way before regular check in time. The room itself was immaculate—beautifully designed, stunning view of the ..."
Reviewed on 6 Jul 2025

The Langham, Chicago
330 North Wabash Avenue, Chicago, IL
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
9.6/10 Exceptional! (1,002 reviews)
"The Langham is quite possibly the best hotel I've ever stayed at. The staff were absolutely amazing and the hotel itself was so clean. The hallways smelled so good too which I know is a weird observation but the wood they used for the floors and doors were so aromatic and it was something my party ..."
Reviewed on 30 Jun 2025

The Peninsula Chicago
108 East Superior Street, Chicago, IL
Stay at this 5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition ...
9.8/10 Exceptional! (1,001 reviews)
"Always a great stay!"
Reviewed on 3 Jul 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.