Hillsboro Vacations from $371

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The Latest Hillsboro vacation packages

Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was $753, price is now $371 per person
$371
per person
Jun 12 - Jun 14
found 19 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,639 reviews)
The room was clean, comfortable, and quiet. My only complaint is that I wish the tv’s would allow for streaming services. They just had normal channels.

Reviewed on May 5, 2026

Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
Save 100% on your flight
Price was $668, price is now $426 per person
$426
per person
Jul 26 - Aug 1
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.4/10 Very Good! (819 reviews)
Room decent but customer service was excellent. Breakfast should be free

Reviewed on May 4, 2026

The Cheshire

The Cheshire

4 out of 5
Save 100% on your flight
Price was $903, price is now $614 per person
$614
per person
Jul 26 - Aug 1
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,006 reviews)
The bar was the perfect spot for a nightcap! Breakfast was also good, though there wasn't much seating available.

Reviewed on Apr 18, 2026

21C Museum Hotel St Louis

21C Museum Hotel St Louis

4.5 out of 5
Downtown West
Save 100% on your flight
Price was $1,037, price is now $734 per person
$734
per person
Jul 26 - Aug 1
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9/10 Wonderful! (1,819 reviews)
Really cool hotel with great onsite bar/restaurant, gym, pool and art gallery.

Reviewed on May 6, 2026

Hilton St. Louis Airport

Hilton St. Louis Airport

3.5 out of 5
Woodson Terrace
Save 100% on your flight
Price was $764, price is now $551 per person
$551
per person
Jul 26 - Aug 1
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
7.6/10 Good! (1,000 reviews)
Overpriced for an old run down hotel. Elevator was broken, hotel room door lower hall large slanted. So much so that you could see under the door so I had to use a towel. Paint chipping and bad plumbing and crumbs in corner common areas meaning they don’t deep vacuum. Breakfast looked good but I did not partake. Bar area was the best as well as the staff there. We checked out ASAP.

Reviewed on May 5, 2026

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Hillsboro Hotel Deals

Historic Red Rooster Inn

Historic Red Rooster Inn

2 out of 5
123 E Seward St Hillsboro IL
9.8/10 Exceptional! (37 reviews)
Yes

Reviewed on Mar 27, 2026

Get rates
Historic Red Rooster Inn
Countryside Inn

Countryside Inn

2 out of 5
8105 IL-127 Hillsboro IL
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $87 total per night from May 8 to May 9
$87 total
May 8 - May 9
Total with taxes and fees
5.8/10 (40 reviews)
The space is excellent and includes more than the usual room--full kitchen, for example. Staff are exceptionally welcoming and skilled.

Reviewed on May 5, 2026

Countryside Inn
Charming Hillsboro Home < 1 Mi to Downtown!

Charming Hillsboro Home < 1 Mi to Downtown!

3 out of 5
Hillsboro IL
10/10 Exceptional! (1 review)
Much nicer then a motel room.

Reviewed on Jun 6, 2025

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Charming Hillsboro Home < 1 Mi to Downtown!
See all 59 properties in Hillsboro
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.

Find the Best Hillsboro Vacation Packages

Hillsboro Essential Information

Language
English
Currency
U.S dollars
Population
5,700
Top Sights
Litchfield Museum and Route 66 Welcome Center, Lake Lou Yeager and Raymond Shoal Creek Golf Course

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Frequently asked questions

How much does a Hillsboro vacation package cost?
You'll find cheap prices from $371 on Expedia for your Hillsboro escape. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Hillsboro costs.
What are the cheapest months to go to Hillsboro?
You can typically find lower rates and better availability in December, January and February. Take a look at our cheap Hillsboro vacation packages and you could score some excellent off-season deals.
How many days is enough for Hillsboro?
The ideal duration for your Hillsboro vacation depends on what you'd like to see and do. Generally, a handful of days to a week will give you time to hit all the top attractions and explore some hidden spots along the way.
How to find the best Hillsboro package deals?
Start your search for a Hillsboro package deal by entering your travel dates and destination under our "Packages" tab. Then select some filters, like "Property type" and "Guest rating," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Hillsboro package deal right away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Hillsboro adventure underway.
Is it cheaper to book a Hillsboro vacation as a package?
You can enjoy significant savings on your Hillsboro retreat by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to view some great hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Hillsboro?
If you have your Hillsboro vacation dates finalized, book as early as you can to bag some incredible deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for setting off on a whim.
Does Expedia offer Book Now, Pay Later Hillsboro vacation packages?
If you're like us, you love traveling but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Hillsboro vacation across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.