Ashton Vacations from $374

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The Latest Ashton vacation packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $594, price is now $374 per person
$374
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!

Reviewed on Feb 2, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,029, price is now $571 per person
$571
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Staff was extremely polite, rooms were clean. No issues at all

Reviewed on Feb 2, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $757, price is now $464 per person
$464
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
There were no glasses in the room to drink out of. There was no lotion. There was no coffee maker. The shower curtain does not stretch the whole way so water gets all over the bathroom. We had a free VIP "hot" breakfast. When went down, there was no hot food. Just coffee and some bakery items. And no employee to serve us. Very, very misleading. We won't be staying here again.

Reviewed on Feb 2, 2026

La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $642, price is now $397 per person
$397
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.

Reviewed on Jan 26, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $717, price is now $481 per person
$481
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (3,098 reviews)
Great rooms and easy check in. Can’t believe I haven’t stayed here before. I’ll be be back!

Reviewed on Feb 4, 2026

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Ashton Hotel Deals

Hampton Inn DeKalb, IL

Hampton Inn DeKalb, IL

3 out of 5
663 S. Annie Glidden Road DeKalb IL
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $110 total per night from Feb 20 to Feb 21
$110 total
Feb 20 - Feb 21
Total with taxes and fees
9.2/10 Wonderful! (1,004 reviews)
The whole facility was great room was clean and roomy. The breakfast was great the biscuits and gravy tasted homemade.

Reviewed on Feb 3, 2026

Hampton Inn DeKalb, IL
Tru By Hilton Dixon

Tru By Hilton Dixon

2.5 out of 5
1806 S. Galena Ave Dixon IL
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $117 total per night from Feb 15 to Feb 16
$117 total
Feb 15 - Feb 16
Total with taxes and fees
8.4/10 Very Good! (59 reviews)
Everything was perfect

Reviewed on Jan 26, 2026

Tru By Hilton Dixon
Home2 Suites by Hilton Dekalb

Home2 Suites by Hilton Dekalb

3 out of 5
575 S ANNIE GLIDDEN RD DeKalb IL
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $157 total per night from Feb 7 to Feb 8
$157 total
Feb 7 - Feb 8
Total with taxes and fees
9.2/10 Wonderful! (414 reviews)
Clean room, modern amenities and kitchenette is so very helpful.

Reviewed on Jan 25, 2026

Home2 Suites by Hilton Dekalb
See all 66 properties in Ashton
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 Ashton Vacation Packages

Ashton Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rockford, IL (RFD-Greater Rockford)
Population
920

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Frequently asked questions

How much does an Ashton vacation package cost?
You'll find cheap prices from $374 on Expedia for your Ashton escape. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Ashton costs.
What are the cheapest months to go to Ashton?
November, December and January are the best times to search for cheap Ashton vacation packages. Opting to travel in less busy periods means you can usually find better prices on flights and accommodations.
How many days is enough for Ashton?
With a well-planned itinerary, you can easily tick off the main Ashton sights in a few days. But if you'd like to explore off the beaten track or go on day tours, consider booking your Ashton vacation for longer.
How to find the best Ashton package deals?
Use Expedia's filters to find some unbeatable Ashton package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Ashton package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book an Ashton vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and stays separately. Better still, you can customize your Ashton escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Ashton?
If you've got your Ashton travel dates confirmed, book early to score some terrific deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for impromptu escapes.
Does Expedia offer Book Now, Pay Later Ashton vacation packages?
Your Ashton break is meant to be an escape from your busy life, not a reason for money worries. So to give you that extra flexibility, we've teamed up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.