Port Barrington Holidays

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Top Flight + Hotel Deals in Port Barrington

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Price was €801, price is now €489 per person
€489
per person
7 Sept - 12 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.4/10 Very good! (3,939 reviews)
Clean, rustic, great. Will visit again.

Reviewed on 17 Jul 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €766, price is now €492 per person
€492
per person
20 Sept - 24 Sept
found 8 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
decent property - definitely shows better in photos. that was probably my biggest let-down. also, only staying one night, the room cleaner came into our room at 8 am despite check out time not being until noon. my kid was still asleep and I was in the shower. front desk service level definitely elevated the rating.

Reviewed on 17 Jul 2026

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
Downtown Chicago
Price was €815, price is now €531 per person
€531
per person
7 Sept - 12 Sept
found 1 day ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.8/10 Excellent! (2,363 reviews)
Very clean room. The front desk person was extremely helpful in giving directions on how to get valet parking.

Reviewed on 17 Jul 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,014, price is now €663 per person
€663
per person
20 Sept - 24 Sept
found 8 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (3,435 reviews)

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €957, price is now €645 per person
€645
per person
20 Sept - 24 Sept
found 8 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (501 reviews)
Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place.

Reviewed on 14 Jul 2026

Top hotels in Port Barrington

Hyatt Regency Deerfield

Hyatt Regency Deerfield

4 out of 5
1750 Lake Cook Rd Deerfield IL
Fully refundableReserve now, pay when you stay
The price is €125 per night from 14 Aug to 15 Aug
€125
14 Aug - 15 Aug
includes taxes & fees
8.8/10 Excellent! (1,064 reviews)
"All was good except the breakfast Buffett staff is a bit unorganized and food needs more flavor."

Reviewed on 17 Jul 2026

Hyatt Regency Deerfield
Sheraton Suites Chicago Elk Grove

Sheraton Suites Chicago Elk Grove

3.5 out of 5
121 Northwest Point Boulevard Elk Grove Village IL
The price is €150 per night from 20 Jul to 21 Jul
€150
20 Jul - 21 Jul
includes taxes & fees
8/10 Very good! (1,002 reviews)
"Very clean and nice rooms"

Reviewed on 16 Jul 2026

Sheraton Suites Chicago Elk Grove
Great Wolf Lodge Illinois

Great Wolf Lodge Illinois

3 out of 5
1700 Nations Dr Gurnee IL
The price is €163 per night from 16 Aug to 17 Aug
€163
16 Aug - 17 Aug
includes taxes & fees
Great Wolf Lodge Illinois
See all 825 properties in Port 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 Port Barrington attractions

Fox River Preserve

7.4/10 (8 reviews)
Explore the great outdoors at Fox River Preserve, a lovely green space in Port Barrington. Stroll along the lakeside or attend a sporting event in the area.
See properties

Frequently asked questions

How much does a Port Barrington holiday package cost?
You can grab a holiday package to this top destination from €489 on Expedia. But how much your holiday to Port Barrington costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Port Barrington?
You can generally find reduced prices and greater availability in January, February and November. Explore our cheap Port Barrington holiday packages and you could score some great off-season discounts.
How many days is enough for Port Barrington?
Typically, a handful of days is enough to check out the main attractions during your Port Barrington holiday. However, if you prefer to have more time to rest or take day tours, consider extending your trip.
How to find the best Port Barrington package deals?
Use Expedia's filters to find some great Port Barrington package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for Port Barrington package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your holiday package as soon as possible.
Is it cheaper to book a Port Barrington holiday as a package?
You can enjoy significant savings on your next Port Barrington getaway by booking a personalised holiday package. Click on the "Package" heading, then enter your travel dates and destination to browse the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Port Barrington?
If you're planning a spur-of-the-moment Port Barrington holiday, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land awesome deals on your hotels and flights by booking well in advance.
How to plan a trip to Port Barrington?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to go to Port Barrington.
  2. Plan your budget wisely: As well as the cost of your hotel, you should consider other expenses. These include food, transportation and flights. Also, set aside some extra funds for unexpected costs that may crop up during your trip to Port Barrington.
  3. Decide how many days away: Start by compiling a list of the activities and sights you'd like to get to in Port Barrington. Then, estimate how long you'll need at each, including any travel time.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to pick a Port Barrington holiday package that brings all your bookings together.

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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.