South Barrington Vacations from $660
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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.
The Latest South Barrington vacation packages
Price found within the past 48 hours. Click for updated prices.
Kimpton Gray Hotel by IHG
Downtown Chicago
$1,181
per person
Nov 3 - Nov 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
The room was very clean and spacious. Staff was very informative about what was accessible during our stay. I would definitely stay here again if I come back to visit Chicago.
Reviewed on Sep 1, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
$1,678
per person
Nov 3 - Nov 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
The Trump Hotel In Chicago is one of my family's FAVORITE hotels in the world. We stay at The Trump every single time we're in Chicago. It's the BEST.😀👍
Reviewed on Sep 2, 2026
Four Seasons Hotel Chicago
Downtown Chicago
$1,137
per person
Nov 5 - Nov 8
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Perfect location for shopping, beach, and restaurants. Very clean and staff is very friendly… did not disappoint. Everything met the mark and expectations of a Four Seasons.
Reviewed on Sep 2, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
$1,159
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
We absolutely loved this hotel. My wife and I came for two days to celebrate my birthday. The location is fantastic to walk many great places, breakfast buffet was the best, excellent selection and tasty. While eating breakfast then brought me a birthday brownie and put chocolate in our room. Above and beyond expectations. Very clean and modern hotel with great staff. Roof top bar is a must!
Reviewed on Sep 2, 2026
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Arboretum of South Barrington
7.8/10 (15 reviews)
This upscale outdoor shopping center offers retail, dining, and entertainment amid lush gardens from its tree farm heritage. Enjoy a movie at Star Cinema Grill or bowling and bocce at Pinstripes.
What to do in South Barrington
Chicago: Willis Tower Skydeck and The Ledge Ticket
$47
per adult
88% of travellers recommend
South Barrington Hotel Deals
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
$251 nightly
$295 total
Sep 27 - Sep 28
Total with taxes and fees
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
$179 nightly
$204 total
Sep 7 - Sep 8
Total with taxes and fees
9/10 Wonderful! (3,105 reviews)
"Clean ,relaxing and helpful staff . Will be returning"
Reviewed on Sep 3, 2026
Marriott Chicago O'Hare
8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
$188 nightly
$221 total
Sep 27 - Sep 28
Total with taxes and fees
8.6/10 Excellent! (1,376 reviews)
"Staff friendly shuttle service was great"
Reviewed on Sep 2, 2026
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.
Find the Best South Barrington Vacation Packages
South Barrington Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Population | 4,600 |
Top Sights | Makray Memorial Golf Club, Deer Grove Forest Preserve and Bakers Lake Nature Preserve |
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Frequently asked questions
How much does a South Barrington vacation package cost?
Offering excellent value package deals from $660 on Expedia, you'll be pleasantly surprised at how much a vacation to South Barrington costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to South Barrington?
If you're looking to book a cheap South Barrington vacation package, consider planning a trip in February, July and October. You'll usually find lower prices on flights and hotels during these months — ideal for a budget-friendly getaway.
How many days is enough for South Barrington?
Generally, a handful of days is enough to see the top sights during your South Barrington vacation. However, if you'd like to have time to kick back or go on day trips, consider extending your trip.
How to find the best South Barrington package deals?
Use Expedia's filters to find some terrific South Barrington package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for South Barrington package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a South Barrington vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking stays and flights individually. Better still, you can customize your South Barrington trip to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to South Barrington?
Land incredible discounts by booking your flights early with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for a spur-of-the-moment South Barrington escape.
Does Expedia offer Book Now, Pay Later South Barrington vacation packages?
If you're like us, you love exploring new places but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your South Barrington break over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
