Port Barrington Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Port Barrington Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Sheraton Grand Chicago Riverwalk
Downtown Chicago
CA $838
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,841 reviews)
We unfortunately came to stay when the staff decided to strike. No room service , no cleaning service for a 4 night stay. Barely got towels on the last day. Disappointing.
The only upside was the location.
Reviewed on Oct 22, 2026
Ready to book your vacation to Port Barrington?
Port Barrington Hotel Deals
Hyatt Regency Deerfield
1750 Lake Cook Rd Deerfield IL
CA $157
CA $177 total
Nov 24 - Nov 25
includes taxes & fees
Comfort Inn & Suites Arlington Heights - Schaumburg
2112 S Arlington Heights Rd Arlington Heights IL
Fully refundable
CA $130
CA $146 total
Nov 24 - Nov 25
includes taxes & fees
8.2/10 Very good! (1,513 reviews)
"This place was so good"
Reviewed on Oct 22, 2026
Motel 6 Rolling Meadows, IL - Chicago Northwest
1800 Winnetka Cir Rolling Meadows IL
Fully refundableReserve now, pay when you stay
CA $79
CA $91 total
Nov 17 - Nov 18
includes taxes & fees
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.
Frequently asked questions
How much does a Port Barrington vacation package cost?
You can pick up a vacation package to this top destination from CA $715 on Expedia. However, how much your vacation to Port Barrington costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Port Barrington?
You can usually find reduced prices and greater availability in January, February and November. Take a look at our cheap Port Barrington vacation packages and you could score some great off-season discounts.
How many days is enough for Port Barrington?
The ideal duration for your Port Barrington vacation depends on what you'd like to do. Typically, a handful of days to a week will give you time to visit all the main attractions and discover some hidden spots along the way.
How to find the best Port Barrington package deals?
Use Expedia's handy filters to help you find some fabulous Port Barrington package deals. When you begin your search, simply 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 browse for Port Barrington package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Port Barrington vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging stays and flights individually. Better still, you can personalize your Port Barrington escape to match your exact needs. Pick 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 vacation package to Port Barrington?
Enjoy incredible bargains by booking your flights early with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Port Barrington getaway.
How to plan a trip to Port Barrington?
- Pick the ideal time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to visit Port Barrington.
- Calculate your budget: Ensure you have enough money to pay for everything from food and transportation to airfares and activities. Your hotel will likely be the biggest expense during your trip to Port Barrington.
- Decide your trip length: Think about how much time you'd like to spend exploring Port Barrington. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a customized Port Barrington vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
