Port Barrington Vacation Packages

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Top Port 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
Save 100% on your flight
per person
Sep 22 - Sep 29
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Staff was great and breakfast buffet was awesome. Highly recommend

Reviewed on Jul. 13, 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 22 - Sep 29
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
This place was secure and beautiful. The amenities were top notch & I felt 100% safe while there. Will return!

Reviewed on Jul. 7, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 22 - Sep 29
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I love Virgin air and expected a 5-star experience. Hotel checkin was not all that welcoming, but efficientl. They had no valet service and basically told us we were on our own. Thought ok I need a drink so went to the rooftop bar. An afterthought at this hotel. Cushions were dirty and faded. Barely staffed. More like a rooftop bar in costs rica than downtown Chicago. Room was nice and stylish. The highlight of the stay tbh as was the coffee shop.

Reviewed on Jul. 13, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 22 - Sep 29
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Amazing customer service

Reviewed on Jul. 13, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 22 - Sep 29
found 2 days ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Nice property, very walkable. Front desk was great. Bar area nice & welcome drink nice. Concierge was not around. Got suite with 2 full baths which was awesome with teens. Great stay overall!

Reviewed on Jul. 12, 2025

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Port Barrington Hotel Deals

Grand Royal Hotel O'Hare - Chicago
Grand Royal Hotel O'Hare - Chicago
3.5 out of 5
1000 Busse Rd, Elk Grove Village, IL
Fully refundableReserve now, pay when you stay
The price is CA $130 per night from Jul 20 to Jul 21
CA $130
CA $147 total
Jul 20 - Jul 21
includes taxes & fees
5.6/10 (109 reviews)
"Cheap and convenient to airports"

Reviewed on Jul. 9, 2025

Grand Royal Hotel O'Hare - Chicago
DoubleTree by Hilton Chicago - Arlington Heights
DoubleTree by Hilton Chicago - Arlington Heights
4 out of 5
75 W Algonquin Rd, Arlington Heights, IL
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from Aug 7 to Aug 8
CA $127
CA $142 total
Aug 7 - Aug 8
includes taxes & fees
8/10 Very Good! (1,015 reviews)
"Polite staff, nice location, clean rooms."

Reviewed on Jul. 11, 2025

DoubleTree by Hilton Chicago - Arlington Heights
Comfort Inn Chicago Schaumburg - O'Hare Airport
Comfort Inn Chicago Schaumburg - O'Hare Airport
2.5 out of 5
1300 E Higgins Rd, Schaumburg, IL
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Jul 28 to Jul 29
CA $122
CA $140 total
Jul 28 - Jul 29
includes taxes & fees
7/10 Good! (860 reviews)
"Cleaning Staff is so kind and polite."

Reviewed on Jul. 1, 2025

Comfort Inn Chicago Schaumburg - O'Hare Airport
See all 774 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

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 $1,213 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.