
Far Southeast Side Adventure Holidays
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Top flight + Adventure hotel deals in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.

Hilton Chicago O'Hare Airport
O'Hare
per person
11 Sept - 16 Sept
found 19 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.2/10 Very Good! (2,069 reviews)
Item was left in room. I tried for days to get contact with front desk and security will little to no luck. They say nothing reported so I consider that as theft by staff. Very disappointing.
Reviewed on 2 Jul 2025

Level Chicago – Old Town
Downtown Chicago
per person
21 Aug - 24 Aug
found 20 hours ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (320 reviews)
This was a wonderful location.
It wasn't a type of stay that I am familiar with, in that, there isn't really a lot of people to reach out to ask for assistance. But, all in all, I would definitely stay there again.
Reviewed on 29 Jun 2025


The Hoxton Chicago
Downtown Chicago
per person
4 Aug - 11 Aug
found 23 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
My husband and I had planned our trip to chicago months ago with our now 8 month old daughter. The plan was to fly up from kansas city to specifically use the rooftop pool at the hotel and enjoy a vacation where we relax in a nice hotel. The trip turned south when we arrive and the front desk told us the pool was closed for the entire weekend due to an issue with another guest, and that they needed to spend the weekend cleaning the pool. I understand things happen, but we made it clear that we came up from Kansas City just to use the pool. The hotel gave us a $150 credit to use at the hotel AFTER I had complained. I didn't feel that the $150 covered any sort of distress I felt from flying my family up to Chicago for a trip where the one amenity was unusable. That $150 did not get us far at the restaurants with the inflated prices of the hotel, which I understand.. My issue is that I didn't feel valued as a guest enough to come to an agreement of compensation that I thought covered what we paid to be at The Hotel. The staff was kind, but we felt like the staff kept saying nothing could be done when I felt so much more could have been done to salvage our trip.
Reviewed on 4 Jul 2025

Hyatt Lodge Oak Brook Chicago
per person
18 Sept - 23 Sept
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.8/10 Excellent! (1,008 reviews)
Parking lot under construction messing amd challenging to get to main entrance. Front desk staff pleasant and very helpful. Inner building lacked clear instruction to locate pool, sauna steam room. Rooms were excellent bed super comfy. Disappointed in breakfast i miss understood i thought set up was brunch. Overall ok nearby Oak Brook mall and fine eatry. Review other spa like lodges before locking into this location. Happy travels....
Reviewed on 3 Jul 2025
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Trump International Hotel & Tower Chicago
Downtown Chicago
per person
4 Sept - 7 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
Amazing hotel with large rooms right off Michigan avenue. Staff is amazing, they are always friendly and helpful.
Reviewed on 27 Jun 2025


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Hotel Riu Plaza Chicago
Downtown Chicago
per person
5 Sept - 8 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,065 reviews)
Really enjoyed our stay at this hotel. Conveniently located, spacious rooms and great buffet style breakfast.
Reviewed on 4 Jul 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
per person
4 Sept - 7 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
Amazing hotel with large rooms right off Michigan avenue. Staff is amazing, they are always friendly and helpful.
Reviewed on 27 Jun 2025

Level Chicago – Old Town
Downtown Chicago
per person
21 Aug - 24 Aug
found 20 hours ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (320 reviews)
This was a wonderful location.
It wasn't a type of stay that I am familiar with, in that, there isn't really a lot of people to reach out to ask for assistance. But, all in all, I would definitely stay there again.
Reviewed on 29 Jun 2025
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Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
per person
15 Sept - 19 Sept
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,058 reviews)
Overall it was a beautiful experience. I had a corner suite on a high floor, and the views of Lake Michigan were absolutely stunning truly a highlight of my stay. The check-in process was smooth and the staff at the front desk were incredibly warm and welcoming.
However, I did have one unfortunate experience that put a damper on an otherwise perfect stay. About two hours before checkout, while I was still in the room getting ready (having just gotten out of the shower), a room service staff member entered without me hearing her knock likely due to the music I had playing. Not only did this feel like a significant intrusion on my privacy, but she also began throwing away my drinks that were still on the table.
When I confronted her, she apologized and explained that she had been told I had already checked out. While I understand mistakes happen, it was disappointing that she continued clearing items even after seeing I was clearly still in the room. It was a frustrating and awkward situation that left a negative impression at the end of an otherwise lovely visit.
With better communication between departments and a bit more sensitivity to guests’ privacy, this stay would have been perfect. I truly loved everything else about the hotel and hope this feedback helps improve the experience for future guests.
Reviewed on 28 Jun 2025


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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.