Valparaiso Vacation Packages

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Your Valparaiso Vacation

The coastal scenery and spectacular views are just the start of the things Valparaiso has on offer. Experience the very best of this fascinating city your way with a personalized Valparaiso vacation package. Make your trip to Valparaiso even more fun and exciting by going sightseeing. Valparaiso University, The Course at Aberdeen and Taltree Arboretum and Gardens are some of the leading attractions you'll want to explore. Browse Expedia's wide range of travel options and begin planning your ideal vacation to Valparaiso now.

Top Valparaiso Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was CA $913, price is now CA $671 per person
CA $671
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything.

Reviewed on Nov 3, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $1,352, price is now CA $941 per person
CA $941
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.

Reviewed on Nov 8, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $1,898, price is now CA $1,336 per person
CA $1,336
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $1,106, price is now CA $794 per person
CA $794
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,284, price is now CA $938 per person
CA $938
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)

Ready to book your vacation to Valparaiso?

 

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Valparaiso Hotel Deals

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 $120 per night from Nov 12 to Nov 13
CA $120
CA $158 total
Nov 12 - Nov 13
includes taxes & fees
8.4/10 Very good! (2,424 reviews)
"Older room. But for the most part clean. Staff very helpful."

Reviewed on Nov 10, 2026

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 $129 per night from Nov 30 to Dec 1
CA $129
CA $162 total
Nov 30 - Dec 1
includes taxes & fees
Ameristar Casino Hotel East Chicago
Spring House Inn

Spring House Inn

2.5 out of 5
303 N Mineral Springs Rd Chesterton IN
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from Nov 18 to Nov 19
CA $128
CA $151 total
Nov 18 - Nov 19
includes taxes & fees
Spring House Inn
See all 1,282 properties in Valparaiso
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.
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Stay near popular Valparaiso attractions

A golf course with a flagstick, sand bunkers, and a tree in the background.

The Course at Aberdeen

7.2/10 (15 reviews)
Enjoy a round of golf in Valparaiso at The Course at Aberdeen. While you're here, you can savor the charming coffeehouses.
See properties

Frequently asked questions

How much does a Valparaiso vacation package cost?
You can grab a vacation package to this popular destination from CA $671 on Expedia. However, how much your vacation to Valparaiso costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Valparaiso?
You can usually find lower rates and better availability in December, January and February. Browse our cheap Valparaiso vacation packages and you could score some great off-season deals.
How many days is enough for Valparaiso?
Typically, a handful of days is enough to tick off the main sights during your Valparaiso vacation. However, if you'd like to have time to kick back or take day trips, think about extending your itinerary.
Is it worth booking a vacation package to Valparaiso?
Boasting a host of highlights starting with its excellent golfing, Valparaiso is a good vacation destination. Whether you want to visit sights such as Memorial Opera House and Chicago Street Theatre or take the path less travelled, you'll have plenty to see and do on your Valparaiso vacation.
How to find the best Valparaiso package deals?
Bagging a cheap Valparaiso package deal is a breeze with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, apply some filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most economical Valparaiso package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Valparaiso vacation as a package?
You can enjoy significant savings on your Valparaiso retreat by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to view the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Valparaiso?
Secure incredible bargains by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Valparaiso getaway.
How to plan a trip to Valparaiso?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Valparaiso.
  2. Set your budget: Factor in costs such as flights, transportation and food when working out how much to put aside for your trip to Valparaiso. Then, pick a hotel that fits your budget, whether that's a low-cost option or a high-end getaway.
  3. Decide how long to go away for: Now that you're more familiar with Valparaiso, you can figure out the right length of your break. Create a rough itinerary and allocate enough time to cover everything you want to do.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find a Valparaiso vacation 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.