South Barrington Holidays

Photo by Erik Rowley

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to €185 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in South Barrington

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was €1,443, price is now €873 per person
€873
per person
4 Oct - 10 Oct
found 10 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Great location and room was fantastic! Only negatives were a lengthy check in and access to the outside deck was closed at 10 PM. Probably a good idea for that, but it would’ve been nice to go out there for a nightcap.

Reviewed on 26 Aug 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was €1,794, price is now €1,081 per person
€1,081
per person
4 Oct - 10 Oct
found 10 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,059 reviews)
Will be coming back! Beautiful rooms and great staff.

Reviewed on 24 Aug 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was €2,271, price is now €1,396 per person
€1,396
per person
2 Nov - 7 Nov
found 22 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was €1,722, price is now €1,066 per person
€1,066
per person
4 Oct - 10 Oct
found 10 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (666 reviews)
The hotel never got cool, hot everywhere, even the community areas. We had to use the TV in the communal area as ours didn't work. We called on day one and the girl laughed and never sent anyone to fix it. Our key cards didn't work multiple times during the stay. The party that happened at the pool on Sunday night of our stay was awful. I couldn't imagine what my kids saw even those this hotel said no parties.

Reviewed on 25 Aug 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was €1,713, price is now €1,117 per person
€1,117
per person
4 Oct - 10 Oct
found 10 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.

Reviewed on 21 Aug 2025

Top hotels in South Barrington

Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road, Chicago, IL
The price is €154 per night from 19 Sept to 20 Sept
€154
19 Sept - 20 Sept
includes taxes & fees
8.4/10 Very Good! (1,125 reviews)
"Great amenities and very clean and friendly staff"

Reviewed on 20 Aug 2025

Marriott Chicago O'Hare
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 €181 per night from 19 Sept to 20 Sept
€181
19 Sept - 20 Sept
includes taxes & fees
8.2/10 Very Good! (2,101 reviews)
Passing Thru
"Nice quiet and convenient hotel and room. Excellent staff."

Reviewed on 24 Aug 2025

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 €140 per night from 19 Sept to 20 Sept
€140
19 Sept - 20 Sept
includes taxes & fees
8.6/10 Excellent! (1,886 reviews)
"Great all over"

Reviewed on 23 Aug 2025

Hyatt Regency O'Hare Chicago
See all 1,113 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.

Popular places to visit

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

Wrigley Field

4.5/5(40 reviews)

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

Wrigley Field
Magnificent Mile - River North showing street scenes, signage and night scenes

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home 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
Navy Pier

Navy Pier

4/5(125 reviews)

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

Navy Pier

What to do in South Barrington

River tour boat in Chicago

Architecture River Tour

€36
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

€35
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

€39
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in South Barrington

Frequently asked questions

How much does a South Barrington holiday package cost?
Offering excellent value package deals from €873 on Expedia, you'll be pleasantly surprised at how much a holiday 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 hoping to book a cheap South Barrington holiday package, consider travelling in January, February and November. You'll generally find better rates on hotels and airfares during these months — perfect for a budget-friendly break.
How many days is enough for South Barrington?
Typically, a handful of days is enough to check out the major attractions during your South Barrington holiday. But if you want to have more time to relax or go on day trips, consider extending your itinerary.
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 holiday package as early as possible.
Is it cheaper to book a South Barrington holiday as a package?
An Expedia holiday package could score you significant savings when compared to booking stays and flights individually. Better still, you can customise 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 holiday 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.
How to plan a trip to South Barrington?

  1. Choose when to travel: Check your diary and get your bags packed. Your favourite season and the available activities will also help you decide when to holiday in South Barrington.
  2. Work out your budget: Ensure you have enough money to pay for everything from meals and transportation to airfares and activities. Your hotel will probably be the largest expense during your trip to South Barrington.
  3. Work out your trip length: Consider how much time you want to spend discovering South Barrington. Plan your days so you can get to all the activities and attractions you're interested in at a leisurely pace.
  4. Combine your accommodation and airfare: After you've settled on your dates and duration, book the perfect South Barrington holiday package for you.

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