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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,371, price is now CA $913 per person
CA $913
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
We will be back. Thank you!!!

Reviewed on Jun 22, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $2,102, price is now CA $1,251 per person
CA $1,251
per person
Jul 28 - Jul 31
just found
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.

Reviewed on Jun 19, 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 $2,439, price is now CA $1,687 per person
CA $1,687
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,557 reviews)
The people at the front desk were extremely helpful. Everyone was super kind & you never really have to leave the hotel.. plenty of shops and restaurants right there in the hotel! Breakfast was not included, but there is breakfast on site.. there’s cheap breakfast and expensive breakfast all depends on what you are in the mood for. Wonderful stay over all!!!

Reviewed on Jun 22, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,746, price is now CA $1,217 per person
CA $1,217
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.

Reviewed on Jun 11, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,740, price is now CA $1,285 per person
CA $1,285
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,327 reviews)
Great location, great space in the rooms!!

Reviewed on Jun 21, 2026

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South Barrington Hotel Deals

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 $180 per night from Jun 28 to Jun 29
CA $180
CA $205 total
Jun 28 - Jun 29
includes taxes & fees
8.8/10 Excellent! (2,705 reviews)
"Just okay"

Reviewed on Jun 22, 2026

Hyatt Regency O'Hare Chicago
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 $359 per night from Jul 3 to Jul 4
CA $359
CA $422 total
Jul 3 - Jul 4
includes taxes & fees
8.4/10 Very good! (2,318 reviews)
"Perfect place to stay when you have an early morning flight the next day."

Reviewed on Jun 22, 2026

Hilton Chicago O'Hare Airport
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 $253 per night from Jul 2 to Jul 3
CA $253
CA $297 total
Jul 2 - Jul 3
includes taxes & fees
8.6/10 Excellent! (1,280 reviews)
"The room had a smell… old carpet I guess. Not much information provided to me about the pool or fitness area My key cards didn’t work- required them to be changed out twice. The second time the guy was a bit snappy with me about it. Besides that guy everyone else was good. Just in general the rooms ..."

Reviewed on Jun 22, 2026

Marriott Chicago O'Hare
See all 1,196 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
A coastal cityscape with high-rise buildings, a marina, and a park area.

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 $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River and Lake Cruise

CA $69
per adult
94% of travellers recommend
Chicago By Night River and Lake Cruise
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.