Barrington Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Your Barrington Vacation

Get ready to experience Barrington your way with a custom Barrington vacation package! Discovering the treasures of this fascinating city is simple with a base in a neighborhood such as Riverwoods, which is great for nature, among lots of other things. Love to explore your new surroundings? Arboretum of South Barrington, Harper College and Deer Park Town Center are three of the leading places to visit during your trip to Barrington. Expedia has what you need to escape your routine. Tailor your vacation to Barrington to match your travel style, whatever that may be!

Top Barrington Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,198, price is now CA $827 per person
CA $827
per person
May 2 - May 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,422 reviews)
Overall the experience was amazing

Reviewed on Mar 5, 2026

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,339, price is now CA $981 per person
CA $981
per person
May 5 - May 8
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
This was a trendy aesthetic hotel. It is in a great location. Had a good time.

Reviewed on Feb 26, 2026

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,528, price is now CA $1,165 per person
CA $1,165
per person
May 2 - May 5
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.4/10 Exceptional! (1,177 reviews)
Very beautiful, clean hotel, and the staff was very respectful and nice

Reviewed on Feb 24, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,293, price is now CA $998 per person
CA $998
per person
May 29 - May 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Had a great stay!! Kelly at the front desk was so sweet

Reviewed on Feb 22, 2026

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was CA $1,334, price is now CA $1,037 per person
CA $1,037
per person
Apr 28 - May 2
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Everything was great

Reviewed on Feb 18, 2026

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

Ready to book your vacation to Barrington?

 

Choose your dates

Barrington Hotel Deals

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 CA $267 per night from Mar 27 to Mar 28
CA $267
CA $314 total
Mar 27 - Mar 28
includes taxes & fees
8.4/10 Very Good! (2,224 reviews)
Yed

Reviewed on Mar 4, 2026

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 CA $173 per night from Mar 8 to Mar 9
CA $173
CA $197 total
Mar 8 - Mar 9
includes taxes & fees
8.8/10 Excellent! (2,385 reviews)
Convenient, great amenities, good food

Reviewed on Mar 5, 2026

Hyatt Regency O'Hare Chicago
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $183 per night from Apr 3 to Apr 4
CA $183
CA $215 total
Apr 3 - Apr 4
includes taxes & fees
8.6/10 Excellent! (1,228 reviews)
The room was nice and the staff was courteous. I would recommend this hotel to friends and family

Reviewed on Mar 1, 2026

Marriott Chicago O'Hare
See all 1,619 properties in 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Barrington

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
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

You can enjoy some retail therapy 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 featuring a sunset and rides

Navy Pier

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

Navy Pier

What to do in Barrington

Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $55
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Color Factory Chicago Ticket

Color Factory Chicago Ticket

CA $47
per adult
96% of travellers recommend
Color Factory Chicago Ticket
cruise ship sailing past navy pier in chicago

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

CA $225
per adult
80% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
See all activities in Barrington

Explore a world of travel with Expedia

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