North Barrington Holidays
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North Barrington Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Save 100% on your flight
Price was S$855, price is now S$461 per person
S$461
per person
6 Jan - 11 Jan
found 19 hours ago
Return direct flight included
Hartford (BDL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
great staff...loved our stay.
Reviewed on 22 Nov, 2025
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was S$1,294, price is now S$728 per person
S$728
per person
6 Jan - 11 Jan
found 19 hours ago
Return direct flight included
Hartford (BDL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Everything was first class, even the coffee shop downstairs. Not to mention the grocery store that is attached to the same building. The ultimate convenience right near the miracle Mile in Chicago, my most favorite place in the world.
Reviewed on 25 Nov, 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was S$884, price is now S$505 per person
S$505
per person
6 Jan - 11 Jan
found 19 hours ago
Return direct flight included
Hartford (BDL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
The room was beautiful and clean and a good city view of the city
Reviewed on 26 Nov, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was S$1,847, price is now S$1,065 per person
S$1,065
per person
6 Jan - 11 Jan
found 19 hours ago
Return direct flight included
Hartford (BDL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Mostly great. The pull out sofa bed is not usable as it’s so uncomfortable. So then they charge $50/night for each rollaway. Thats not a good solution.
Reviewed on 28 Nov, 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was S$1,002, price is now S$620 per person
S$620
per person
6 Jan - 11 Jan
found 19 hours ago
Return direct flight included
Hartford (BDL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
I thoroughly enjoyed my time at Pendry Chicago. I stayed in a tower king room. I originally was going to stay in a suite but the normal king room was very spacious for one person. The valet service was pretty quick and the valets were all very nice. The front desk clerk was extremely helpful and professional. I loved staying right on Michigan Ave and within walking distance to so many things. I read some reviews saying safety was a concern but I didn’t experience any safety issues. They lock the doors on Michigan Ave after a certain point to keep the flow of traffic thru a better monitored entrance. I also took an evening(beginning around 9:30pm) stroll around Millennium Park, down to Buckingham fountain and back up Michigan Ave to the river and the surroundings blocks around the hotel. At no point did I feel unsafe and would highly recommend this hotel to anyone coming to Chicago. The location is fantastic, the employees are amazing and the rooms are comfy. What more could you ask for?
Reviewed on 26 Nov, 2025
Top hotels in North Barrington
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$298 per night from 19 Dec to 20 Dec
S$298
19 Dec - 20 Dec
includes taxes & fees
8.2/10 Very Good! (2,181 reviews)
Convenient. Wonderful staff. Expensive!
Reviewed on 27 Nov, 2025
Holiday Inn Chicago O'Hare – Rosemont by IHG
6600 Mannheim Road, building 2 Rosemont IL
Fully refundable
The price is S$143 per night from 1 Dec to 2 Dec
S$143
1 Dec - 2 Dec
includes taxes & fees
8.8/10 Excellent! (2,624 reviews)
Our flight got delayed and checked in after 2am but staff was nice and welcoming. Only down side was we weren’t informed about water stopped by water construction in the morning from 10am. Checkout time was noon and we got in late so about time to take a shower, there was no shower. They should told ...
Reviewed on 26 Nov, 2025
DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
1200 N Mittel Blvd Wood Dale IL
Fully refundableReserve now, pay when you stay
The price is S$140 per night from 6 Dec to 7 Dec
S$140
6 Dec - 7 Dec
includes taxes & fees
8/10 Very Good! (1,032 reviews)
Room spotless. Staff just perfect.
Reviewed on 23 Nov, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Popular places to visit
Deer Park Town Center
You can do some window-shopping at Deer Park Town Center during your stay in Deer Park. Stroll along the lakeside or attend a sporting event in this quaint area.
Fox River Preserve
Explore the great outdoors at Fox River Preserve, a lovely green space in Port Barrington. Stroll along the lakeside or attend a sporting event in the area.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
