South Side Scuba Diving Holidays

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Top flight + Scuba Diving hotel deals in South Side

Price found within the past 48 hours. Click for updated prices.
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

Downtown Chicago
£1,027
per person
21 Dec - 28 Dec
found 1 hour ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (2,414 reviews)
One staff member stood out . Her name was Shanika . She helped me navigate during a stressful morning. She gave me good direction in how to get to my half marathon after my uber ride didn't show up. Explained different methods of public transportation and where to find it. If it wasn't for her I wouldn't have made my race and I would have been in Chicago for. I reason. Grateful for great staff !!!

Reviewed on 12 Oct 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,071
per person
21 Dec - 28 Dec
found 1 hour ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
The Riu was great. I especially liked their attention to low-energy use. And, yes, like other commenters stated, the breakfast was plentiful.

Reviewed on 12 Oct 2026

Kinzie Hotel

Kinzie Hotel

Downtown Chicago
£1,073
per person
21 Dec - 28 Dec
found 1 hour ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (2,187 reviews)
Great

Reviewed on 12 Oct 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
£1,237
per person
1 Dec - 7 Dec
found 13 hours ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
Eurostars Magnificent Mile

Eurostars Magnificent Mile

Downtown Chicago
£1,047
per person
21 Dec - 28 Dec
found 1 hour ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9/10 Wonderful! (3,934 reviews)
Hands-down, always my favorite place to stay when I am in Chicago. I’ve been staying here for years. It’s essentially located so you can walk everywhere to the magnificent mile to the Gold Coast Beach to all of the shopping. Restaurants are right next to it. There is a true food, kitchen and a soul cycle right next to it as well and Tal nightclub is also right next-door. The staff is absolutely amazing in the rooms are luxurious for a great price.

Reviewed on 12 Oct 2026

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5* Scuba Diving holidays in South Side

Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
£1,331
per person
19 Dec - 22 Dec
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,991
per person
23 Nov - 27 Nov
found 19 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Great place to stay. It’s a beautiful place to stay in downtown Chicago

Reviewed on 12 Oct 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
£2,383
per person
23 Nov - 27 Nov
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 Scuba Diving holidays in South Side

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
£925
per person
19 Dec - 22 Dec
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,727 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,167
per person
19 Dec - 22 Dec
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Great place to stay. It’s a beautiful place to stay in downtown Chicago

Reviewed on 12 Oct 2026

Pendry Chicago

Pendry Chicago

Downtown Chicago
£949
per person
19 Dec - 22 Dec
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,163 reviews)
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4 Night Scuba Diving holidays in South Side

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£1,038
per person
28 Dec - 1 Jan
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
Place was great in general 10/10 will be back

Reviewed on 12 Oct 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,068
per person
28 Dec - 1 Jan
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
The Riu was great. I especially liked their attention to low-energy use. And, yes, like other commenters stated, the breakfast was plentiful.

Reviewed on 12 Oct 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,991
per person
23 Nov - 27 Nov
found 19 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Great place to stay. It’s a beautiful place to stay in downtown Chicago

Reviewed on 12 Oct 2026

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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

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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.