Northwest Side Luxury Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Flight and Luxury hotel deals in Northwest Side
Hotel Riu Plaza Chicago
Reviewed on Aug 31, 2026
Swissotel - Chicago
Reviewed on Aug 31, 2026
5* Luxury holidays in Northwest Side
The Peninsula Chicago
Reviewed on Aug 25, 2026
3 Night Luxury holidays in Northwest Side
Hotel Riu Plaza Chicago
Reviewed on Aug 31, 2026
Swissotel - Chicago
Reviewed on Aug 31, 2026
4 Night Luxury holidays in Northwest Side
Swissotel - Chicago
Reviewed on Aug 31, 2026
Hotel Riu Plaza Chicago
Reviewed on Aug 31, 2026
Plan the perfect luxury Northwest Side vacation with Expedia
What are some benefits when booking luxury Northwest Side vacations?
When you book a luxury Northwest Side vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax.
How can I find all-inclusive luxury vacations in Northwest Side?
If you're looking for something luxurious in Northwest Side, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together.
Can I book a cheap luxury vacation?
While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $1,003, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 26. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first.
Are there luxury spa vacations?
Yes, luxury spa vacations are available and quite popular in Northwest Side. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search.
What should I look for in a luxury family vacation in Northwest Side?
When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Northwest Side.
Can I book last-minute luxury vacations?
Yes, last-minute bookings are often available in Northwest Side. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces.
What can help me find the best luxury vacation deals in Northwest Side?
You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Northwest Side or travelling to more obscure destinations altogether can often lead to lower prices.
Can I book a luxury vacation that is fully refundable?
Yes, fully refundable reservations are sometimes available on luxury vacation packages in Northwest Side. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking.
Why should I book my luxury vacation with Expedia?
When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings.
Things to do
Wendella's Lake and River Architecture Tour
Wendella's 90-min Chicago River Architecture Tour
More vacations you might like
Top Luxury Vacation Destinations
- Luxury vacations in Portugal
- Luxury vacations in India
- Luxury vacations in France
- Luxury vacations in Switzerland
- Luxury vacations in Canada
- Luxury vacations in Jamaica
- Luxury vacations in Italy
- Luxury vacations in New Zealand
- Luxury vacations in the Maldives
- Luxury vacations in Costa Rica
- Luxury vacations in Florida Keys
- Luxury vacations in Mexico
- Luxury vacations in the Caribbean
- Luxury vacations in Zanzibar
- Luxury vacations in Cancun
- Luxury vacations in Kerala
- Luxury vacations in Australia
- Luxury vacations in Puglia
- Luxury vacations in Cuba
- Luxury vacations in Cyprus
