South Barrington Holidays

Photo by Erik Rowley

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Top Flight + Hotel Deals in South Barrington

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Sept - 11 Sept
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9/10 Wonderful! (324 reviews)
Finding a park is hard and the process of getting a room is very tedious but still very beautiful I’ve been twice

Reviewed on 29 Jul 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
6 Sept - 13 Sept
found 9 hours ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
The hotel was nice, staff were friendly and the overall stay was excellent and convenient to walk.

Reviewed on 28 Jul 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Sept - 11 Sept
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
The hotel is in a fantastic location. Staff service was very high quality and the lobby and common areas were very clean and well organized. Gym was modern, big and clean. The actual room had some marks on the walls and a buzzy air handling vent in the master. An automated lighting system that was a bit dim and difficult to use. We would stay again. Mini bar and snacks were high quality. We would stay again.

Reviewed on 29 Jul 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Sept - 11 Sept
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9.4/10 Exceptional! (3,357 reviews)
The room was luxurious and pleasant. Location perfect for reaching any activity whether on business or personal visit. Love it!! ❤️💃

Reviewed on 28 Jul 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Sept - 11 Sept
found 1 day ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on 22 Jul 2025

Top hotels in South Barrington

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 €182 per night from 22 Aug to 23 Aug
€182
22 Aug - 23 Aug
includes taxes & fees
8/10 Very Good! (2,084 reviews)
"Convenient location in the airport, quick blue line train access. Nice bar and restaurant, friendly and helpful staff."

Reviewed on 27 Jul 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 €133 per night from 25 Aug to 26 Aug
€133
25 Aug - 26 Aug
includes taxes & fees
8.6/10 Excellent! (1,800 reviews)
"The front desk was really nice I appreciated them and the stay ."

Reviewed on 26 Jul 2025

Hyatt Regency O'Hare Chicago
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 €125 per night from 10 Aug to 11 Aug
€125
10 Aug - 11 Aug
includes taxes & fees
8.6/10 Excellent! (2,350 reviews)
"The staff was very helpful."

Reviewed on 28 Jul 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
See all 1,130 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

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

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

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
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 holiday package cost?
Offering excellent value package deals from €720 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.