Far Southeast Side Adventure Holidays

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Top flight + Adventure hotel deals in Far Southeast Side

Price found within the past 48 hours. Click for updated prices.
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago
£851
per person
20 Nov - 25 Nov
found 13 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (3,269 reviews)
The Emily Hotel

The Emily Hotel

Downtown Chicago
£1,423
per person
26 Oct - 31 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
The staff was super helpful and the room was clean and beautiful!

Reviewed on 16 Sept 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,150
per person
24 Oct - 27 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Love the the hotel, great location.

Reviewed on 17 Sept 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
£1,120
per person
1 Nov - 5 Nov
found 18 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (561 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£1,117
per person
24 Oct - 27 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
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5* Adventure holidays in Far Southeast Side

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

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,208
per person
1 Dec - 4 Dec
found 14 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
£2,525
per person
26 Oct - 31 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The hotel is located in a prime location with shops and restaurants nearby. The staff was very accommodating and helpful.

Reviewed on 15 Sept 2026

Waldorf Astoria Chicago

Waldorf Astoria Chicago

Downtown Chicago
£2,091
per person
1 Nov - 5 Nov
found 18 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)
Very nice hotel With beautiful rooms

Reviewed on 14 Sept 2026

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3 Night Adventure holidays in Far Southeast Side

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

Hotel Riu Plaza Chicago

Downtown Chicago
£996
per person
1 Dec - 4 Dec
found 14 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Love the the hotel, great location.

Reviewed on 17 Sept 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£1,117
per person
24 Oct - 27 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
Pendry Chicago

Pendry Chicago

Downtown Chicago
£1,242
per person
24 Oct - 27 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,146 reviews)
The gym was great. The noise from the road was very loud.

Reviewed on 15 Sept 2026

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4 Night Adventure holidays in Far Southeast Side

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

The Talbott, Autograph Collection

Downtown Chicago
£860
per person
26 Nov - 30 Nov
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (165 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,005
per person
26 Nov - 30 Nov
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Love the the hotel, great location.

Reviewed on 17 Sept 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
£1,120
per person
1 Nov - 5 Nov
found 18 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (561 reviews)
Don't see what you're looking for?
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

£35
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Far Southeast 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.