South Side Ski Holidays

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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
€1,801
per person
8 Oct - 14 Oct
found 16 hours ago
Return flight included
Athens (ATH) to Chicago (ORD)
8.2/10 Very good! (2,899 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
€2,315
per person
20 Sept - 25 Sept
found 7 hours ago
Return direct flight included
Tirana (TIA) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.

Reviewed on 12 Aug 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
€1,995
per person
8 Oct - 14 Oct
found 16 hours ago
Return flight included
Athens (ATH) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
It was a good stay. Views, room cleaning everyday and convenient, but you will spend a lot going back and forth to the magnificent mile. No pool but has a Ferris wheel . I recommend.

Reviewed on 17 Aug 2026

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

Downtown Chicago
€2,312
per person
8 Oct - 14 Oct
found 16 hours ago
Return flight included
Athens (ATH) to Chicago (ORD)
9.4/10 Exceptional! (2,311 reviews)
Very close to everything.

Reviewed on 17 Aug 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

Downtown Chicago
€2,009
per person
8 Oct - 14 Oct
found 1 day ago
Return flight included
Athens (ATH) to Chicago (ORD)
9/10 Wonderful! (3,779 reviews)
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Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
€2,185
per person
20 Sept - 25 Sept
found 7 hours ago
Return direct flight included
Tirana (TIA) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
This is an excellent 5 star hotel. So accommodating in every way possible. This is the second time I have stayed at this Chicago property.

Reviewed on 16 Aug 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
€3,286
per person
20 Sept - 25 Sept
found 7 hours ago
Return direct flight included
Tirana (TIA) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Nobu Hotel Chicago

Nobu Hotel Chicago

Downtown Chicago
€3,362
per person
8 Oct - 14 Oct
found 16 hours ago
Return flight included
Athens (ATH) to Chicago (ORD)
9.4/10 Exceptional! (897 reviews)
Rooms and beds are always so nice. Very calming and always get a good night’s sleep. I’ve always had a great experience. One detail which falls short is the toilet paper is very rough. Aside from this detail everything else surpasses my expectations.

Reviewed on 16 Aug 2026

Don't see what you're looking for?
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Price found within the past 48 hours. Click for updated prices.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago
€1,154
per person
17 Sept - 21 Sept
found 16 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,808 reviews)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
€1,337
per person
17 Sept - 21 Sept
found 16 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
It was a good stay. Views, room cleaning everyday and convenient, but you will spend a lot going back and forth to the magnificent mile. No pool but has a Ferris wheel . I recommend.

Reviewed on 17 Aug 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

Downtown Chicago
€1,229
per person
17 Sept - 21 Sept
found 18 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (3,779 reviews)
Don't see what you're looking for?
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€24
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

€21
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

€35
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in South Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.