Far Southwest Side Mountain Holidays

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Top flight + Mountain hotel deals in Far Southwest 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
£1,087
per person
19 Nov - 24 Nov
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,727 reviews)
Need some more food options

Reviewed on 18 Oct 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,598
per person
19 Nov - 24 Nov
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
The Emily Hotel

The Emily Hotel

Downtown Chicago
£1,228
per person
22 Dec - 28 Dec
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,347 reviews)
A party bus pulls up to the

Reviewed on 18 Oct 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
£1,214
per person
22 Dec - 28 Dec
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (576 reviews)
I liked the whirlpool

Reviewed on 18 Oct 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
£1,208
per person
22 Dec - 28 Dec
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
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5* Mountain holidays in Far Southwest Side

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

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,598
per person
19 Nov - 24 Nov
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

Downtown Chicago
£2,164
per person
1 Jan - 6 Jan
found 23 hours ago
Return flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
£2,198
per person
22 Dec - 28 Dec
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
Loved the hotel

Reviewed on 15 Oct 2026

Don't see what you're looking for?
See all available trips from Edinburgh to Far Southwest Side
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3 Night Mountain holidays in Far Southwest Side

Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
£895
per person
23 Nov - 26 Nov
found 6 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
Clean room. Valet service slow.

Reviewed on 18 Oct 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,239
per person
23 Nov - 26 Nov
found 6 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£919
per person
23 Nov - 26 Nov
found 6 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
It was a great location

Reviewed on 18 Oct 2026

Don't see what you're looking for?
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4 Night Mountain holidays in Far Southwest Side

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
£860
per person
19 Nov - 23 Nov
found 5 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
8.2/10 Very good! (3,105 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,350
per person
19 Nov - 23 Nov
found 5 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
£1,026
per person
19 Nov - 23 Nov
found 5 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Don't see what you're looking for?
See all available trips from Edinburgh to Far Southwest Side
View all trips

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 Far Southwest Side

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Where to go when
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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.