Valparaiso Holidays

Photo by Lawrence Tellez

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Top Flight + Hotel Deals in Valparaiso

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was €1,303, price is now €843 per person
€843
per person
2 Nov - 9 Nov
found 6 hours ago
Return direct flight included
Faro (FAO) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Modern comfortable hotel in a good location close to downtown parks and museums Friendly helpful staff Many good restaurants nearby

Reviewed on 19 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €2,651, price is now €1,575 per person
€1,575
per person
2 Nov - 9 Nov
found 6 hours ago
Return direct flight included
Faro (FAO) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was €2,018, price is now €1,253 per person
€1,253
per person
2 Nov - 9 Nov
found 6 hours ago
Return direct flight included
Faro (FAO) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
Rooms are basic and bathrooms and sink area small. But all comfortable

Reviewed on 17 Aug 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was €1,413, price is now €924 per person
€924
per person
2 Nov - 9 Nov
found 6 hours ago
Return direct flight included
Faro (FAO) to Chicago (ORD)
9/10 Wonderful! (335 reviews)
Great property. Outstanding all the way around.

Reviewed on 13 Aug 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was €1,879, price is now €1,239 per person
€1,239
per person
2 Nov - 9 Nov
found 6 hours ago
Return direct flight included
Faro (FAO) to Chicago (ORD)
9.4/10 Exceptional! (1,033 reviews)
Loved the atmosphere and friendly atmosphere

Reviewed on 18 Aug 2025

Top hotels in Valparaiso

Holiday Inn Express Valparaiso by IHG

Holiday Inn Express Valparaiso by IHG

2.5 out of 5
1251 Silhavy Rd, Valparaiso, IN
Fully refundable
The price is €122 per night from 24 Aug to 25 Aug
€122
24 Aug - 25 Aug
includes taxes & fees
8.4/10 Very Good! (735 reviews)
"Excellent breakfast"

Reviewed on 15 Aug 2025

Holiday Inn Express Valparaiso by IHG
Super 8 by Wyndham Valparaiso

Super 8 by Wyndham Valparaiso

2 out of 5
3005 John Howell Dr, Valparaiso, IN
Fully refundableReserve now, pay when you stay
The price is €80 per night from 26 Aug to 27 Aug
€80
26 Aug - 27 Aug
includes taxes & fees
7.2/10 Good! (957 reviews)
"Great place. Comfortable, clean, great service. Could have used more options at the breakfast bar but would truly recommend again"

Reviewed on 23 Jul 2025

Super 8 by Wyndham Valparaiso
Country Inn & Suites by Radisson, Valparaiso, IN

Country Inn & Suites by Radisson, Valparaiso, IN

3 out of 5
2020 Laporte Ave, Valparaiso, IN
Fully refundable
The price is €126 per night from 31 Aug to 1 Sept
€126
31 Aug - 1 Sept
includes taxes & fees
8.4/10 Very Good! (997 reviews)
Nice facility.
"Breakfast was the typical prepared food as served in most motels. The food was ok but nothing fantastic. The room was very clean and the staff was very friendly."

Reviewed on 10 Aug 2025

Country Inn & Suites by Radisson, Valparaiso, IN
See all 1,182 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.

Frequently asked questions

How much does a Valparaiso holiday package cost?
You'll find cheap prices from €843 on Expedia for your Valparaiso getaway. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your holiday to Valparaiso costs.
What are the cheapest months to go to Valparaiso?
You're likely to find lower rates and greater availability in December, January and February. Explore our cheap Valparaiso holiday packages and you could score some excellent off-season deals.
How many days is enough for Valparaiso?
Generally, a handful of days is enough to see the top sights during your Valparaiso holiday. But if you want to have more time to chill out or take day tours, consider extending your trip.
Is it worth booking a holiday package to Valparaiso?
Known for its golfing and home to leading attractions like Memorial Opera House, a Valparaiso holiday is sure to leave an impression. Another highlight to check out? Don't miss Chicago Street Theatre.
How to find the best Valparaiso package deals?
Use Expedia's filter tool to find some unbeatable Valparaiso package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or look for Valparaiso package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your holiday package well in advance.
Is it cheaper to book a Valparaiso holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component individually. And you'll still have the flexibility to create a customised Valparaiso holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday package to Valparaiso?
If you're considering an impromptu Valparaiso getaway, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to Valparaiso?

  1. Pick the right time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to go to Valparaiso.
  2. Set a budget: Factor in expenses like flights, transportation and food when calculating how much to set aside for your trip to Valparaiso. Then, choose a property that suits your budget, whether that's a low-cost stay or a swankier getaway.
  3. Work out your trip length: Think about how long you'd like to spend exploring Valparaiso. Plan your itinerary so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a personalised Valparaiso holiday package.

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