South Barrington Holidays

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Top Flight + Hotel Deals in South Barrington

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Chicago - Magnificent Mile by IHG

Holiday Inn Express Chicago - Magnificent Mile by IHG

2.5 out of 5
Downtown Chicago
Price was €1,008, price is now €755 per person
€755
per person
20 Sept - 25 Sept
found 10 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.4/10 Very good! (1,190 reviews)
Incredibly experience for what you get. The elevator was also broken so we got to carry our luggage up and down 6 flights of stairs or wait an eon for the one available elevator. The water was cold when I went to shower and didn’t warm for twenty minutes. It was a pretty stressful stop on our road trip after driving 14 hours. We wanted a place to relax. The only good things were the location and the beds were comfortable.

Reviewed on 31 Jul 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was €1,227, price is now €869 per person
€869
per person
20 Sept - 25 Sept
found 10 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (3,732 reviews)
Great location I’m the middle of downtown.

Reviewed on 31 Jul 2026

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was €1,122, price is now €944 per person
€944
per person
20 Sept - 25 Sept
found 10 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.4/10 Very good! (2,355 reviews)

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 €6,186, price is now €5,428 per person
€5,428
per person
7 Oct - 13 Oct
found 1 day ago
Return direct flight included
Athens (ATH) to Chicago (ORD)
9.4/10 Exceptional! (2,606 reviews)
Parking was way too expensive and hard to understand

Reviewed on 31 Jul 2026

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Downtown Chicago
Price was €6,563, price is now €5,813 per person
€5,813
per person
7 Oct - 13 Oct
found 1 day ago
Return direct flight included
Athens (ATH) to Chicago (ORD)
9.2/10 Wonderful! (2,325 reviews)

Top hotels in South Barrington

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 €167 per night from 30 Aug to 31 Aug
€167
30 Aug - 31 Aug
includes taxes & fees
Hyatt Regency O'Hare Chicago
DoubleTree by Hilton Lisle Naperville

DoubleTree by Hilton Lisle Naperville

4 out of 5
3003 Corporate West Dr Naperville IL
Fully refundableReserve now, pay when you stay
The price is €83 per night from 12 Aug to 13 Aug
€83
12 Aug - 13 Aug
includes taxes & fees
DoubleTree by Hilton Lisle Naperville
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 €128 per night from 24 Aug to 25 Aug
€128
24 Aug - 25 Aug
includes taxes & fees
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
See all 1,221 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.

Stay near popular South Barrington attractions

Arboretum of South Barrington

7.8/10 (15 reviews)
This upscale outdoor shopping centre offers retail, dining, and entertainment amid lush gardens from its tree farm heritage. Enjoy a film at Star Cinema Grill or bowling and bocce at Pinstripes.
See properties

What to do in South Barrington

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€24
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

€21
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

€35
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in South Barrington

Frequently asked questions

How much does a South Barrington holiday package cost?
Offering excellent value package deals from €755 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.