South Side Mountain Holidays

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Top flight + Mountain hotel deals in South Side

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£895
per person
14 Dec - 18 Dec
found 12 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
This was my first stay at a Hotel Riu and I was thoroughly impressed! It reminded me of the hotels in Southeast Asia I have visited - attentive staff, very clean facilities, attention to details, and the best breakfast buffet I have probably ever had at a US hotel that is included in the hotel room rate. The bonus to all of this being that it was literally steps from the Magnificent Mile and had easy access to Express bus lines and the MTA. Would definitely stay here again!

Reviewed on 5 Oct 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,363
per person
14 Dec - 18 Dec
found 12 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Hands down the best hotel in Chicago!

Reviewed on 5 Oct 2026

The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

Downtown Chicago
£1,431
per person
28 Dec - 2 Jan
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The hotel was beautiful, the room was comfortable, and the staff was welcoming and attentive. Everything was clean and well maintained, and the location made it easy to get around the city. Overall, it was a really nice stay and I’d definitely consider coming back.

Reviewed on 24 Sept 2026

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile

Downtown Chicago
£1,167
per person
28 Dec - 2 Jan
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,643 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
£2,108
per person
7 Dec - 11 Dec
found 19 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
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5* Mountain holidays in South Side

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,410
per person
16 Nov - 20 Nov
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Hands down the best hotel in Chicago!

Reviewed on 5 Oct 2026

The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

Downtown Chicago
£1,431
per person
28 Dec - 2 Jan
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The hotel was beautiful, the room was comfortable, and the staff was welcoming and attentive. Everything was clean and well maintained, and the location made it easy to get around the city. Overall, it was a really nice stay and I’d definitely consider coming back.

Reviewed on 24 Sept 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
£2,108
per person
7 Dec - 11 Dec
found 19 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
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3 Night Mountain holidays in South Side

Price found within the past 48 hours. Click for updated prices.
Chez Hotel Arlington Heights

Chez Hotel Arlington Heights

£783
per person
13 Nov - 16 Nov
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9/10 Wonderful! (848 reviews)
It was our first time staying there, and we were aware of other guests’ reviews regarding noise and events at the hotel. Luckily, the wedding and event noise did not bother us. However, we can understand why some guests complained about the thin walls and ceilings. We stayed on the second floor, which was far enough away from the noise, so we had a comfortable stay. Other than that, we did experience the usual issue you can encounter at any hotel: some guests simply don’t seem to care about others and slammed their doors even at 3 a.m. That’s not really the hotel’s responsibility, though. Noise caused by inconsiderate guests depends on the people staying there and, to some extent, luck. What we really liked was the interior and overall design of the hotel. Most importantly, our room was very comfortable and exceptionally clean. You can tell that someone put a lot of thought into the interior design and layout. The larger TV screen, nice lighting, and high ceilings really made a difference and made the room feel more spacious and comfortable. We appreciated these thoughtful details.

Reviewed on 5 Oct 2026

Eaglewood Resort and Spa

Eaglewood Resort and Spa

£808
per person
13 Nov - 16 Nov
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
8.8/10 Excellent! (1,353 reviews)
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare
£972
per person
13 Nov - 16 Nov
found 1 day ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
8.6/10 Excellent! (2,530 reviews)
The staff is wonderful!!!! And hotel is clean.

Reviewed on 5 Oct 2026

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4 Night Mountain holidays in South Side

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,363
per person
14 Dec - 18 Dec
found 12 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Hands down the best hotel in Chicago!

Reviewed on 5 Oct 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
£1,419
per person
15 Nov - 19 Nov
found 5 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Room was dated and showed signs of hard wear; front desk staff unfriendly; door men never once open the door for us from the street; area around hotel dirty. Shay, the concierge was super nice though and the lobby was attractively decorated.

Reviewed on 4 Oct 2026

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago
£1,441
per person
15 Nov - 19 Nov
found 5 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (3,324 reviews)
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

£32
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in South Side

More 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.