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 Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was €1,182, price is now €723 per person
€723
per person
13 Nov - 19 Nov
found 5 hours ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9/10 Wonderful! (1,975 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.

Reviewed on 25 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €2,320, price is now €1,397 per person
€1,397
per person
13 Nov - 19 Nov
found 5 hours ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.

Reviewed on 25 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,734, price is now €1,057 per person
€1,057
per person
13 Nov - 19 Nov
found 5 hours ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on 22 Aug 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €1,489, price is now €975 per person
€975
per person
13 Nov - 19 Nov
found 5 hours ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
Slow elevators. Solid hotel but nothing spectacular. Would choose other properties in this price point next time.

Reviewed on 26 Aug 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was €1,287, price is now €852 per person
€852
per person
13 Nov - 19 Nov
found 5 hours ago
Return flight included
Thessaloniki (SKG) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on 27 Aug 2025

Top hotels in Port Barrington

DoubleTree by Hilton Libertyville - Mundelein

DoubleTree by Hilton Libertyville - Mundelein

4 out of 5
510 E IL Route 83, Mundelein, IL
Fully refundableReserve now, pay when you stay
The price is €107 per night from 28 Sept to 29 Sept
€107
28 Sept - 29 Sept
includes taxes & fees
DoubleTree by Hilton Libertyville - Mundelein
Motel 6 Elk Grove Village, IL

Motel 6 Elk Grove Village, IL

2 out of 5
1000 W Devon Ave, Elk Grove Village, IL
Fully refundableReserve now, pay when you stay
The price is €46 per night from 15 Sept to 16 Sept
€46
15 Sept - 16 Sept
includes taxes & fees
Motel 6 Elk Grove Village, IL
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 €115 per night from 12 Sept to 13 Sept
€115
12 Sept - 13 Sept
includes taxes & fees
Hyatt Regency Deerfield
See all 756 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.

Popular places to visit

Makray Memorial Golf Club

Enjoy a round of golf in Barrington at Makray Memorial Golf Club. Stroll along the lakeside or attend a sporting event in this quaint area.

Makray Memorial Golf Club

Baker's Lake Nature Preserve

Explore the great outdoors at Baker's Lake Nature Preserve, a lovely green space in Barrington. Amble around this romantic area's lakeside or attend a sporting event.

Baker's Lake Nature Preserve

The Catlow Theater

You can make plans for a show at The Catlow Theater on your trip to Barrington. Stroll along the lakeside or attend a sporting event in this family-friendly area.

The Catlow Theater

Frequently asked questions

How much does a Port Barrington holiday package cost?
You can grab a holiday package to this top destination from €723 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.

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