Porter Beach Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Christina Blust

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Porter Beach

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Price was CA $1,033, price is now CA $686 per person
CA $686
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,653 reviews)
Good area to walk around

Reviewed on Sep 9, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,442, price is now CA $1,443 per person
CA $1,443
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
We picked the Trump Hotel-Chicago to celebrate our 35th Wedding Anniversary mainly for the location and the amenities. The hotel EXCEEDED our expectations in every way. (1) The staff is so warm, kind, compassionate and extremely professional in such a friendly down-to-earth way. (2) The property itself is immaculate. (3) The amenities: Terrace 16- the view will take your breath away! The food/cocktails were fabulous as was the service. (3) Pablo - Director of Rooms, Curtis -Concierge were off the charts fabulous. I wish I could remember all the staff names that went out of their way to make our weekend so special. I cannot wait to stay here again. As another reviewer said: put any political opinions aside and treat yourself to a stay here. YOU WILL LOVE IT. (There is no political aura here...only a fantastic team that wants you to enjoy your stay and they go out of their way to make sure you do).

Reviewed on Sep 8, 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was CA $1,346, price is now CA $823 per person
CA $823
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
Wonderful hotel and great atmosphere!

Reviewed on Sep 10, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was CA $1,364, price is now CA $852 per person
CA $852
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,844 reviews)
Had an important meeting and was expecting the restaurant to be open on time at 7:00am…it opened at 7:20….very convenient place…one staff could have been nicer and more welcoming…felt like a burden when we checked in

Reviewed on Sep 9, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $2,413, price is now CA $1,541 per person
CA $1,541
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.6/10 Exceptional! (1,001 reviews)
Got pick pocketed in the elevator. I really like this hotel. Plan to return.

Reviewed on Sep 8, 2025

Porter Beach Hotel Deals

Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

Porter
Get rates
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

3.5 out of 5
777 Blue Chip Drive, Michigan City, IN
Fully refundableReserve now, pay when you stay
The price is CA $125 per night from Sep 16 to Sep 17
CA $125
CA $160 total
Sep 16 - Sep 17
includes taxes & fees
Blue Chip Casino Hotel and Spa
Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

4 out of 5
777 Ameristar Blvd., East Chicago, IN
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Sep 14 to Sep 15
CA $135
CA $165 total
Sep 14 - Sep 15
includes taxes & fees
Ameristar Casino Hotel East Chicago
See all 1,100 properties in Porter Beach
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 Porter Beach vacation package cost?
The cheapest Porter Beach package is CA $686, so your dream trip can become a reality — without it costing a fortune. Bundle flights, hotels and car rentals to build a package that matches your traveling style.
How do I get a cheap travel package to Porter Beach?
Combine your hotel and flight bookings, add on extras such as activities, and save with a Porter Beach vacation package. You won't just walk away with amazing discounts on your escape — you'll have loads of choice at your fingertips too. When you book with Expedia, you can choose from more than 550 airlines and 1,000,000 hotels across the globe. Your next affordable adventure begins right here, right now!
How far in advance should I book my Porter Beach vacation?
It depends on the airline, but it's usually possible to compare international fares on Expedia up to 12 months in advance. While it's generally recommended to book ahead of time, lucky travelers will occasionally nab a cheaper ticket just weeks prior to the date of departure.
What does an Expedia Porter Beach travel package include?
Travel packages include hotels, rental cars and flights, but you can mix and match them to create your ideal Porter Beach trip. You can also add on fun things like activities and experiences once you've made your booking. You're the boss! When you bundle your bookings with Expedia, you'll enjoy deals you won't find anywhere else.
What should I know before booking a Porter Beach travel package?
Our prices are already low. However, you'll score even better deals if you book your hotels, flights and car rentals together. With an Expedia package, you'll always get transparent pricing and tons of choice.
Can I choose my airline with a Porter Beach Expedia vacation package?
Most definitely. We offer more than 550 partner airlines globally, so you can design your Porter Beach escape according to your travel preferences.
If I'm not able to travel, can I cancel my Porter Beach vacation package?
Your situation can change suddenly, so yes, you can. You may be able to change or cancel your Porter Beach vacation package at no cost if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still make changes, but your airline, hotel or car rental company may impose a fee. Want more information? Look up our Customer Service Portal. We'll help make sure your trip goes off without a hitch.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.