Valparaiso Holidays

Photo by Lawrence Tellez

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Valparaiso Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
27 Sept - 29 Sept
found 11 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
No refrgerator, can hear the noise coming from the street. Room us clean and smell good

Reviewed on 14 Jul, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
27 Sept - 29 Sept
found 11 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
9.2/10 Wonderful! (1,769 reviews)
The location is great, with a fantastic staff and an easy check-in process. I can walk to almost everything, and the bus station is right next to the door.

Reviewed on 16 Jul, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
27 Sept - 29 Sept
found 11 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
Great location, but the $50.00 early check-in fee is ridiculous. Also, the comforter on the bed has seen better days.

Reviewed on 15 Jul, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
27 Sept - 29 Sept
found 11 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I loved the location of the property, and the overall concept of something fun and funky, but I had a "higher end" room, and it was right near the elevator, so I got a lot of noise on that side, plus the El from the other side. The rug wasn't super clean (although the bedding and the rest of the room were a delight). The most annoying thing was the TV. Anything I turned it to, 10 minutes later to the minute, it went back to the Virgin channel #1, here are all our hotels in the world. I really hated having to stay on top of a show, when usually I want the tv on as background while I'm getting ready, etc. Also, this hotel's amenities were oversold, i.e., good luck getting on the rooftop, especially if you just wanted a quiet sip of a drink. I loved the cafe and the staff, though, everyone was very pleasant.

Reviewed on 15 Jul, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
Downtown Chicago
per person
27 Sept - 29 Sept
found 11 hours ago
Return flight included
New York (LGA) to Chicago (ORD)
8.4/10 Very Good! (3,506 reviews)
Awesome location! Everyone was very friendly!

Reviewed on 16 Jul, 2025

Top hotels in 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 S$182 per night from 27 Jul to 28 Jul
S$182
27 Jul - 28 Jul
includes taxes & fees
8.6/10 Excellent! (976 reviews)
"Had a great stay here! Building was clean and room was pretty big for a basic room. The free breakfast was really great! Waffle makers, little cheese omelettes, and bacon. Convenient Dairy Queen and Culver’s right next door for food was nice too. Staff very friendly and helpful. Recommend!"

Reviewed on 15 Jul, 2025

Country Inn & Suites by Radisson, Valparaiso, IN
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 S$121 per night from 27 Jul to 28 Jul
S$121
27 Jul - 28 Jul
includes taxes & fees
7.2/10 Good! (946 reviews)
"Convenient location"

Reviewed on 6 Jul, 2025

Super 8 by Wyndham Valparaiso
Hampton Inn & Suites Valparaiso

Hampton Inn & Suites Valparaiso

2.5 out of 5
1451 Silhavy Rd, Valparaiso, IN
Fully refundableReserve now, pay when you stay
The price is S$206 per night from 27 Jul to 28 Jul
S$206
27 Jul - 28 Jul
includes taxes & fees
8.6/10 Excellent! (739 reviews)
Stay here!
"Young girl at check in, think her name was Katie, was super friendly to all guests. Hotel looked brand new and was quite comfortable"

Reviewed on 3 Jul, 2025

Hampton Inn & Suites Valparaiso
See all 1,188 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 S$437 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.