Far Southeast Side Cheap Holidays

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

The Talbott, Autograph Collection

Downtown Chicago
HK$5,861
per person
25 Nov - 29 Nov
found 7 hours ago
Return flight included
Baltimore (BWI) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
HK$9,457
per person
25 Nov - 29 Nov
found 7 hours ago
Return flight included
Baltimore (BWI) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Hands down the best hotel in Chicago!

Reviewed on 5 Oct 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
HK$6,406
per person
25 Nov - 29 Nov
found 7 hours ago
Return flight included
Baltimore (BWI) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
This was my first stay at a Hotel Riu and I was thoroughly impressed! It reminded me of the hotels in Southeast Asia I have visited - attentive staff, very clean facilities, attention to details, and the best breakfast buffet I have probably ever had at a US hotel that is included in the hotel room rate. The bonus to all of this being that it was literally steps from the Magnificent Mile and had easy access to Express bus lines and the MTA. Would definitely stay here again!

Reviewed on 5 Oct 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
HK$6,231
per person
25 Nov - 29 Nov
found 7 hours ago
Return flight included
Baltimore (BWI) to Chicago (ORD)
9.2/10 Wonderful! (1,346 reviews)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
HK$6,455
per person
25 Nov - 29 Nov
found 7 hours ago
Return flight included
Baltimore (BWI) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Room was dated and showed signs of hard wear; front desk staff unfriendly; door men never once open the door for us from the street; area around hotel dirty. Shay, the concierge was super nice though and the lobby was attractively decorated.

Reviewed on 4 Oct 2026

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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
Save 100% on your flight
HK$9,457
per person
25 Nov - 29 Nov
found 7 hours ago
Return flight included
Baltimore (BWI) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Hands down the best hotel in Chicago!

Reviewed on 5 Oct 2026

Don't see what you're looking for?
See all available trips from Columbus to Far Southeast Side
View all trips
Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
HK$4,530
per person
25 Nov - 28 Nov
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
HK$4,646
per person
25 Nov - 28 Nov
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
This was my first stay at a Hotel Riu and I was thoroughly impressed! It reminded me of the hotels in Southeast Asia I have visited - attentive staff, very clean facilities, attention to details, and the best breakfast buffet I have probably ever had at a US hotel that is included in the hotel room rate. The bonus to all of this being that it was literally steps from the Magnificent Mile and had easy access to Express bus lines and the MTA. Would definitely stay here again!

Reviewed on 5 Oct 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
HK$4,715
per person
25 Nov - 28 Nov
found 1 day ago
Return flight included
New York (NYC) to Chicago (ORD)
9.2/10 Wonderful! (1,346 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Far Southeast Side
View all trips
Price found within the past 48 hours. Click for updated prices.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
HK$5,861
per person
25 Nov - 29 Nov
found 7 hours ago
Return flight included
Baltimore (BWI) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
HK$9,457
per person
25 Nov - 29 Nov
found 7 hours ago
Return flight included
Baltimore (BWI) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Hands down the best hotel in Chicago!

Reviewed on 5 Oct 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
HK$6,406
per person
25 Nov - 29 Nov
found 7 hours ago
Return flight included
Baltimore (BWI) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
This was my first stay at a Hotel Riu and I was thoroughly impressed! It reminded me of the hotels in Southeast Asia I have visited - attentive staff, very clean facilities, attention to details, and the best breakfast buffet I have probably ever had at a US hotel that is included in the hotel room rate. The bonus to all of this being that it was literally steps from the Magnificent Mile and had easy access to Express bus lines and the MTA. Would definitely stay here again!

Reviewed on 5 Oct 2026

Don't see what you're looking for?
See all available trips from Columbus to Far Southeast Side
View all trips

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

HK$191
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

HK$314
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

HK$332
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
See all activities in Far Southeast Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.