Far North Side Adults Only Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Flight and Adults Only hotel deals in Far North Side

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

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
Breakfast was the best I have ever had at a hotel!!

Reviewed on Aug. 7, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Loved the attention to details that made the experience exceptional.

Reviewed on Aug. 6, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Oct 17 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Everything is nice specially stuff hosptality

Reviewed on Aug. 8, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,149 reviews)
Moments after arriving the hotel room, I took a shower and when I got out, there was a cockroach on my floor near the bed.

Reviewed on Aug. 7, 2025

Art Villa

Art Villa

5 out of 5
West Town
per person
Oct 17 - Oct 22
found 18 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
10/10 Exceptional! (1 review)
Don't see what you're looking for?
See all available trips from Columbus to Far North Side
View all trips

5* Adults Only holidays in Far North Side

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

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Oct 17 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Everything is nice specially stuff hosptality

Reviewed on Aug. 8, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Loved the attention to details that made the experience exceptional.

Reviewed on Aug. 6, 2025

Art Villa

Art Villa

5 out of 5
West Town
per person
Oct 17 - Oct 22
found 18 hours ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
10/10 Exceptional! (1 review)
Don't see what you're looking for?
See all available trips from Columbus to Far North Side
View all trips

3 Night Adults Only holidays in Far North Side

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

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
Breakfast was the best I have ever had at a hotel!!

Reviewed on Aug. 7, 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
Check in was smooth. The young lady at the front desk was kind, professional and very helpful. The aesthetics of the property is phenomenal. Everything is clean and beautiful.

Reviewed on Aug. 8, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Everything is nice specially stuff hosptality

Reviewed on Aug. 8, 2025

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

4 Night Adults Only holidays in Far North Side

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
O'Hare
per person
Sep 26 - Sep 30
found 9 hours ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
8.8/10 Excellent! (2,250 reviews)
The room we stayed at was very clean however the air conditioner was extremely noisy.

Reviewed on Aug. 8, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Oct 17 - Oct 21
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Everything is nice specially stuff hosptality

Reviewed on Aug. 8, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Loved the attention to details that made the experience exceptional.

Reviewed on Aug. 6, 2025

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

More vacations you might like

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