Barrington Vacation Packages

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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.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $1,161, price is now CA $787 per person
CA $787
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (116 reviews)
We thoroughly enjoyed our stay. The location was excellent, conveniently close to everything we needed. The room was spacious and spotless. The breakfast was fantastic, offering a wide variety of options to choose from.

Reviewed on May 17, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,919, price is now CA $1,699 per person
CA $1,699
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (480 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.

Reviewed on May 22, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,741, price is now CA $1,702 per person
CA $1,702
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (478 reviews)
Minimum effort. Pleasant stay. Very quiet. Enjoyed the 8th floor common area. Service at the front desk was really great. Convenient coffee shop / bakery in the lobby.

Reviewed on May 18, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,549, price is now CA $997 per person
CA $997
per person
Aug 5 - Aug 9
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,332 reviews)
They were extremely accommodating! Highly recommend.

Reviewed on May 26, 2026

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 CA $1,806, price is now CA $1,221 per person
CA $1,221
per person
Aug 5 - Aug 9
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,507 reviews)
Clean and have a beautiful view of the lake

Reviewed on May 26, 2026

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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 $338 per night from Jun 21 to Jun 22
CA $338
CA $397 total
Jun 21 - Jun 22
includes taxes & fees
8.4/10 Very Good! (2,309 reviews)
"Conveniently located near Terminal 1 and 2 at OHare; staff extremely kind and helpful. Food available inside hotel until 12 midnight."

Reviewed on May 25, 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 $233 per night from May 28 to May 29
CA $233
CA $266 total
May 28 - May 29
includes taxes & fees
8.8/10 Excellent! (2,576 reviews)
"Everything is perfect. Clean room, clean hotel and safe too."

Reviewed on May 26, 2026

Hyatt Regency O'Hare Chicago
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
6600 Mannheim Road, building 2 Rosemont IL
Fully refundable
The price is CA $186 per night from Jun 21 to Jun 22
CA $186
CA $215 total
Jun 21 - Jun 22
includes taxes & fees
9/10 Wonderful! (2,968 reviews)
"We love staying here when we have an early morning flight out of Chicago O’Hare airport. Having the restaurant right there is wonderful so you don’t have to leave the hotel to grab a bite. We have eaten there for dinners and the food has been really good."

Reviewed on May 26, 2026

Holiday Inn Chicago O'Hare – Rosemont by IHG
See all 1,648 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
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Discover the most popular places to visit in Barrington

Wrigley Field

Wrigley Field

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
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 Barrington

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $31
per child
98% of travellers recommend
Flyover in Chicago
See all activities in Barrington

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