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.
Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,986 reviews)
For a four star hotel in chicago it is very pricy only good for location as the amenities and extras are what you gt in a 3 star hotel outside of the city. The carpet is dated and dusty, the bathroom was clean and more modern than expected, but it is not as expected.

Reviewed on Jul. 16, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 22 - Sep 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
Nice property but very loud at night.

Reviewed on Jul. 17, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Beautiful boutique hotel in the heart of Chicago with exceptional customer service.

Reviewed on Jul. 16, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Beautiful and upscale property

Reviewed on Jul. 17, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
Amazing place overall

Reviewed on Jul. 15, 2025

Ready to book your vacation to South Barrington?

 

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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 $197 per night from Aug 6 to Aug 7
CA $197
CA $224 total
Aug 6 - Aug 7
includes taxes & fees
8.6/10 Excellent! (1,741 reviews)
"Generally a very nice hotel. Escalators to lower level with not working all weekend making it difficult for people with mobility issues."

Reviewed on Jul. 15, 2025

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 $245 per night from Aug 8 to Aug 9
CA $245
CA $288 total
Aug 8 - Aug 9
includes taxes & fees
8/10 Very Good! (2,090 reviews)
"Very convenient. Connected on lower level with the terminal 2. Dated decor. Old bathrooms."

Reviewed on Jul. 16, 2025

Hilton Chicago O'Hare Airport
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
5440 N River Rd, Rosemont, IL
Fully refundable
The price is CA $174 per night from Aug 10 to Aug 11
CA $174
CA $198 total
Aug 10 - Aug 11
includes taxes & fees
8.6/10 Excellent! (2,289 reviews)
"My husband and I stayed in mid-June for the 1st Annual Midwest Convention (held onsite), and while the event was great, the hotel’s accessibility and amenities were seriously lacking. There was insufficient parking for wheelchair users, which created immediate challenges. My husband is in a wheelchair, ..."

Reviewed on Jul. 13, 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
See all 1,124 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in South Barrington

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

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

Wrigley Field
Navy Pier

Navy Pier

4.5/5(459 reviews)

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

Navy Pier
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

4.5/5(19 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue

What to do in South Barrington

River tour boat in Chicago

Architecture River Tour

CA $67
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $62
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in South Barrington

Frequently asked questions

How much does a South Barrington vacation package cost?
You can pick up a vacation package to this popular destination from CA $742 on Expedia. But how much your vacation to South Barrington costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to South Barrington?
January, February and November are great times to look for cheap South Barrington vacation packages. Travelling in quieter months means you can usually find reduced prices on accommodations and flights.
How many days is enough for South Barrington?
Usually, a handful of days is enough to go to the top attractions during your South Barrington vacation. However, if you'd like to have more time to kick back or go on day trips, think about extending your itinerary.
How to find the best South Barrington package deals?
Start your search for a South Barrington package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect South Barrington package deal right away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your South Barrington escape underway.
Is it cheaper to book a South Barrington vacation as a package?
You can enjoy significant savings on your next South Barrington break by booking a personalized vacation package. Click on the "Package" heading, then select your destination and travel dates to see some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to South Barrington?
If you're planning a spontaneous South Barrington adventure, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find incredible deals on your flights and hotels by booking ahead.
How to plan a trip to South Barrington?

  1. Choose when to get away: Check your schedule and pack your bags. Your favourite season and the activities available will also help you decide when to vacation in South Barrington.
  2. Budget wisely: On top of the price of your accommodations, you should factor in other expenses too. These include transportation, flights and food. Also, put aside some extra funds for unexpected costs that may come up during your trip to South Barrington.
  3. Set the duration of your trip: Start by compiling a list of the sights and activities you'd like to get to in South Barrington. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a South Barrington vacation package that brings all your bookings together.

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