A bar area with multiple screens displaying content, a customer notice sign, and a wine rack.
Photo by Erik Rowley
Open Photo by Erik Rowley

South Barrington Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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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.
  • A cityscape at dusk with illuminated skyscrapers, a river, and a bridge.
    Jan 7 - Jan 11

    Swissotel - Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.0/10 - Wonderful (3,566 reviews)
    "Breakfast was good"
    Reviewed November 4, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $1,051
    CA $758
    per traveller
    found 1 day ago
    Swissotel - Chicago
  • A cityscape with modern high-rise buildings, a river, and a bridge.
    Dec 19 - Dec 23

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.6/10 - Excellent (1,875 reviews)
    Roundtrip • Hamilton (YHM) - Chicago (ORD)
    YHM - ORD • 1 stop ORD - YHM • 1 stop
    CA $2,739
    CA $1,191
    per traveller
    found 1 day ago
    Sheraton Grand Chicago Riverwalk
  • A modern living room with a sofa, chairs, a coffee table, and a TV. A large window offers a view of a cityscape and a tower.
    Dec 27 - Jan 2

    Park Hyatt Chicago + Flight

    Downtown Chicago
    6 nights
    5.0 star property
    9.6/10 - Exceptional (1,001 reviews)
    "Given the price point and other reviews, we came here expecting a luxury stay similar to the Waldorf Astoria, Four Seasons, and Peninsula, which are some of our favorite properties to stay at. However, everything from the service and cleanliness to the ambiance of the entrance and lobby and the amenities (other than the gym, which was excellent) is best described as an upgraded version of an average Hilton, Hyatt, or Marriott. For example, there was a hair in the bed. When we reported it, the..."
    Reviewed November 4, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    Save 100% on your flight
    CA $3,612
    CA $2,536
    per traveller
    found 1 day ago
    Park Hyatt Chicago
  • A modern lobby with a sofa, coffee table, and potted plants.
    Jan 7 - Jan 11

    The Emily Hotel + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (1,357 reviews)
    "Our stay at The Emily Hotel was outstanding! The entire property was well-maintained and the customer service provided by Leo and his team was excellent! We thoroughly enjoyed the offerings at Flora and were able to experience a Rooftop Cinema event! The hotel is conveniently located in walking distance to great restaurants and the L. I highly recommend The Emily Hotel and look forward to my stay during my next visit to Chicago!"
    Reviewed November 4, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $1,190
    CA $853
    per traveller
    found 1 day ago
    The Emily Hotel
  • A modern living room with a grey sofa, a round coffee table with a plant, and a TV mounted on the wall.
    Jan 7 - Jan 11

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (602 reviews)
    "If you are looking to stay in a condo type setting, this may be your spot. I checked in which you need to go through a process that takes 15 minutes, (do it before) and they automatically add a $25 per night fee for their gym and roof top. This was NOT published on Hotels.com or any other site. A total rip off as this is not a spa. There was no housekeeping. Checking in took 15 minutes in which there was little to no Wifi, so I had to go do this outside (crazy?). Do the check-in before..."
    Reviewed November 4, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $1,044
    CA $760
    per traveller
    found 1 day ago
    Level Chicago Fulton Market

Discover the most popular places to visit in South Barrington

Arboretum of South Barrington

7.8/10 (15 reviews)
You can do some window-shopping at Arboretum of South Barrington during your stay in South Barrington. Stroll along the lakeside or attend a sporting event in this quaint area.
See properties

South Barrington Hotel Deals

A spacious lobby with a central seating area, a reception desk, and a display of amenities.

Hilton Garden Inn Hoffman Estates

Hilton Garden Inn Hoffman Estates
3.0 star property
2.4 km from South Barrington
9.0 out of 10, Wonderful, (1,000 reviews)
"Staff was amazing... there was one guy at night, not very good, maybe going through something not my business, everyone else was amazing. Luis opened the kitchen and did everything he could to accommodate"
The price is CA $143
CA $162 total
includes taxes & fees
Nov 12 - Nov 13
Hilton Garden Inn Hoffman Estates
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.
See all properties 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 $758 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.