Far Southeast Side Cheap Holidays
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Top flight + Cheap hotel deals in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Downtown Chicago
Price was £1,413, price is now £1,143 per person
£1,143
per person
25 Dec - 30 Dec
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
The hotel lobby and rooftop are nice but the rooms are okay. We had 3 rooms and the shower pressure was terrible in all. The king room felt small so we switched to 2 queens which was much better. The service was so good though and it’s attached to a mall. It was good overall but probably won’t stay here again.
Reviewed on 29 Oct 2026
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View all trips5* Cheap holidays in Far Southeast Side
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View all trips3 Night Cheap holidays in Far Southeast Side
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View all trips4 Night Cheap holidays in Far Southeast Side
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Pendry Chicago
Downtown Chicago
Price was £1,320, price is now £1,090 per person
£1,090
per person
26 Dec - 30 Dec
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.
Reviewed on 8 Nov 2026
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View all tripsThings to do
Skydeck Chicago at Willis Tower
£32
per adult
84% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
£30
per adult
94% of travellers recommend
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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.
