Central Chicago Adventure Vacations

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Flight and Adventure hotel deals in Central Chicago

Price found within the past 48 hours. Click for updated prices.
The Emily Hotel

The Emily Hotel

Downtown Chicago
CA $1,177
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
Save 100% on your flight
CA $1,271
per person
Nov 14 - Nov 18
found 9 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (527 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
CA $1,692
per person
Nov 5 - Nov 8
found 3 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,502
per person
Nov 5 - Nov 8
found 3 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
CA $1,212
per person
Nov 5 - Nov 8
found 3 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (178 reviews)
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5* Adventure holidays in Central Chicago

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

Nobu Hotel Chicago

Downtown Chicago
CA $1,199
per person
Nov 29 - Dec 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (922 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
CA $1,692
per person
Nov 5 - Nov 8
found 3 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

Downtown Chicago
CA $1,273
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,001 reviews)
The hotel was beautiful, the room was comfortable, and the staff was welcoming and attentive. Everything was clean and well maintained, and the location made it easy to get around the city. Overall, it was a really nice stay and I’d definitely consider coming back.

Reviewed on Sep 24, 2026

Don't see what you're looking for?
See all available trips from Columbus to Central Chicago
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3 Night Adventure holidays in Central Chicago

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

The Talbott, Autograph Collection

Downtown Chicago
CA $1,212
per person
Nov 5 - Nov 8
found 3 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (178 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
CA $1,692
per person
Nov 5 - Nov 8
found 3 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.6/10 Exceptional! (2,025 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,502
per person
Nov 5 - Nov 8
found 3 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Central Chicago
View all trips

4 Night Adventure holidays in Central Chicago

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

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,214
per person
Nov 19 - Nov 23
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
CA $1,270
per person
Nov 14 - Nov 18
found 9 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (573 reviews)
Great stay in an elegant mostly residential building. Smooth check in, but had to fill out a few forms. Very nice staff. Young building with lots of dogs yay!

Reviewed on Sep 24, 2026

Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
Save 100% on your flight
CA $1,271
per person
Nov 14 - Nov 18
found 9 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (527 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Central Chicago
View all trips

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $34
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Flyover in Chicago

Flyover in Chicago

CA $53
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in Central Chicago

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.