South Barrington Vacation Packages

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Your South Barrington Vacation

Get ready to experience South Barrington on your terms with a custom South Barrington vacation package! Discovering the best parts of this city is made easier with a base in a neighborhood such as Medinah, which is great for golfing, among other things. If your trip to South Barrington includes some sightseeing, take in popular attractions like Arboretum of South Barrington, Deer Grove Forest Preserve and Makray Memorial Golf Club. No matter your travel plans or budget, organizing a tailored South Barrington vacation is a piece of cake with Expedia.

Top South Barrington Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Chicago Marriott Suites Deerfield

Chicago Marriott Suites Deerfield

4 out of 5
Price was CA $916, price is now CA $670 per person
CA $670
per person
Jun 18 - Jun 22
found 23 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.6/10 Excellent! (1,000 reviews)
I booked this property after a day at O'Hare airport and multiple flight cancellations. I was greeted and checked in efficiently, had a drink and dinner and retired to a very comfortable and clean room. Breakfast the next day consusted of an excellent omelet. Overall a very comfortable and well appointed hotel. Thank you!

Reviewed on Mar 16, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was CA $1,871, price is now CA $1,241 per person
CA $1,241
per person
May 24 - May 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
The room was clean, spacious, with good views.

Reviewed on Apr 12, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,895, price is now CA $1,259 per person
CA $1,259
per person
Jun 18 - Jun 21
found 5 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Breakfast and parking not included

Reviewed on Apr 12, 2026

Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was CA $1,118, price is now CA $768 per person
CA $768
per person
Jun 29 - Jul 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,013 reviews)
Le Meridien Exxex Chicago is in the perfect location, steps from where I need to be when visiting Chicago. The staff are super helpful and friendly. The restaurant serves delicious food and the waitstaff is attentive. Keep up the good work!

Reviewed on Apr 3, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,075, price is now CA $1,522 per person
CA $1,522
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (453 reviews)
What a view!! We loved the apartment! Got to feel like we were living in Chicago for a couple of nights!

Reviewed on Apr 12, 2026

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South Barrington Hotel Deals

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $345 per night from May 9 to May 10
CA $345
CA $405 total
May 9 - May 10
includes taxes & fees
8.4/10 Very Good! (2,275 reviews)
I would rate this hotel as good to excellent if not for one employee. I stayed two nights and all the staff including front desk, restaurant and housekeeping were customer friendly and efficient with one exception. I returned back to the main entrance of the hotel on the second night after a long ...

Reviewed on Apr 12, 2026

Hilton Chicago O'Hare Airport
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $215 per night from Apr 27 to Apr 28
CA $215
CA $245 total
Apr 27 - Apr 28
includes taxes & fees
8.8/10 Excellent! (2,495 reviews)
A bit older and there was work ongoing so it might be better soon. Slightly dingy for a Hyatt atm.

Reviewed on Apr 13, 2026

Hyatt Regency O'Hare Chicago
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $275 per night from May 9 to May 10
CA $275
CA $323 total
May 9 - May 10
includes taxes & fees
8.6/10 Excellent! (1,237 reviews)
amenities were great and the Staff was welcoming.

Reviewed on Apr 9, 2026

Marriott Chicago O'Hare
See all 1,216 properties in South Barrington
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.
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Discover the most popular places to visit in South Barrington

Wrigley Field

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in South Barrington

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in South Barrington

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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.