
West Side Cheap Vacations
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Top Cheap vacation packages in West Side

The Royal Sonesta Chicago Downtown
Reviewed on Oct 22, 2025


Trump International Hotel & Tower Chicago
Reviewed on Oct 20, 2025

Park Hyatt Chicago
Reviewed on Oct 20, 2025

Waldorf Astoria Chicago
Reviewed on Oct 23, 2025
5* Cheap vacations in West Side

Park Hyatt Chicago
Reviewed on Oct 20, 2025

Trump International Hotel & Tower Chicago
Reviewed on Oct 20, 2025

Waldorf Astoria Chicago
Reviewed on Oct 23, 2025
3 Night Cheap vacations in West Side

The Royal Sonesta Chicago Downtown
Reviewed on Oct 22, 2025


Trump International Hotel & Tower Chicago
Reviewed on Oct 20, 2025
4 Night Cheap vacations in West Side

The Blackstone, Autograph Collection
Reviewed on Oct 20, 2025

Level Chicago – Old Town
Reviewed on Oct 22, 2025

Find amazing cheap vacations in West Side
How can I find budget-friendly West Side vacation packages on Expedia?
Playing around with the easy-to-use search wizard is one of the best ways to find affordable West Side vacation packages on Expedia. Tap your dates in and it'll offer some of the cheapest West Side getaways within seconds. You can also use the maximum price filter to view deals within your budget. If you're traveling during peak season dates, it's a good idea to book early to snag some of the best offers. You may score irresistible last-minute specials for travel in low season.
How to find cheap last-minute West Side travel deals?
On Expedia's last-minute travel deals page, you'll encounter a plethora of special offers for late vacations to West Side. Remember, you're more likely to bag savings on last-minute travel during off-peak periods. Consider checking different departure dates, too. Expedia's nifty search tool lets you compare some of the best last-minute West Side vacation packages. The handy filters let you tailor your trip according to your preferences, including hotel star rating, amenities, and property location.
When is the best time to visit West Side on a budget?
For some of the cheapest vacation packages to West Side from $248, it's best to travel during low season dates. With fewer people traveling during these periods, flights and hotels usually have lower prices. It's also a good idea to avoid popular travel times. These include spring break, Thanksgiving, and other federal holidays. On Expedia, you'll encounter some of the best travel deals to West Side. Best of all, vacation payment plans mean you can spread the cost of your trip over 3, 6, or 12 months.
Can I cancel my West Side vacation package booking?
Yes, many of Expedia's cheap West Side getaway packages allow for free cancellation in case your plans change. Follow the easy steps to cancel by logging into your Expedia account and clicking on “Trips” page'. Keep in mind, though, that each vacation package has different cancellation policies, so be sure to look over them before booking. The good news is you'll clearly see this information on Expedia when you book. There's even a free cancellation search filter that lets you view flexible vacations to West Side.
Why should I book my West Side vacation with Expedia?
A multitude of exclusive travel deals you won't find anywhere else is one of the top reasons to book your cheap West Side vacation package with Expedia. And with one of the widest choices of flights and hotels available, you'll easily find the right trip for you. The handy search wizard and filters let you compare hundreds of great deals in seconds, too. It's not only the cheap prices either: Expedia's booking protection and 24/7 support give you peace of mind before and during your 2025 trip.
How to find cheap West Side vacation packages on Expedia?
When searching for budget vacations to West Side, look out for the green savings label. This indicates you've snagged a deal only available on Expedia. Another popular way of getting money off your 2025West Side vacation is by joining One Key. Expedia's amazing reward program gives you access to hundreds of member-only discounts on select hotels. Keep a look out for the blue savings label in the search results. Best of all, One Key is free to join.
Why should I book a package to West Side?
You'll often snag package savings on your West Side vacation when bundling together your flights and accommodation. Expedia even shows you how much you're saving by booking a package. It's not just cheaper prices, either. Packages often have more flexible booking conditions, meaning you're more likely to get a refund in case your 2025 plans change. While booking flights and hotels separately usually requires full payment, West Side vacation packages often let you pay a small upfront deposit to confirm.
How to plan a cheap vacation to West Side?
Settling on your dates is usually the first step to planning an affordable West Side getaway. If you're traveling during peak season dates, it's a good idea to book your trip in advance. This way, you're more likely to bag early-bird deals. Don't rule out a last-minute travel deal for low season dates, though. Once you've picked your dates, tap them into the search wizard to see some of the best West Side vacation package deals. Hop over to Expedia's vacation planning page for more tips for your dream vacation.
Top Cheap West Side Hotels

Hyatt House Chicago Medical/University District
I didn’t get the chance to make it to breakfast.
Reviewed on Oct 18, 2025

Chicago Parthenon Hostel
One of the nicest hostels I’ve stayed in. Rooms and shared spaces were clean, guest population was diverse, kind, and mostly quiet.
Reviewed on Oct 18, 2025

Grand Hostel
I chose a private, double room although i was travelling alone. It was really spacious with a separate cupboard for my case and clothes.The room was very clean and the bed was absolutely devine. So, so comfy. I shared a bathroom with other guests but had no issues at all. The bathroom was top notch ...
Reviewed on Oct 21, 2025