Paoli Vacations from $519

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The Latest Paoli vacation packages

Price found within the past 48 hours. Click for updated prices.
The Chicago Hotel Collection - Wrigleyville

The Chicago Hotel Collection - Wrigleyville

3.5 out of 5
Lakeview
Save 100% on your flight
Price was $766, price is now $519 per person
$519
per person
Sep 1 - Sep 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7/10 Good! (1,023 reviews)
Not a traditional hotel but there was someone at the front desk to help with the check in process. Great location no complaints

Reviewed on Jun 19, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,222, price is now $790 per person
$790
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.

Reviewed on Jun 11, 2026

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
Price was $1,665, price is now $1,111 per person
$1,111
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,557 reviews)
Usually this is one of the best property but this time they had water pipe burst and elevators werent working because of that. It was very inconvinient for this stay.

Reviewed on Jun 20, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,101, price is now $738 per person
$738
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,391 reviews)
Great hotel, would definitely stay here again!

Reviewed on Jun 21, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,371, price is now $932 per person
$932
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,019 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.

Reviewed on Jun 19, 2026

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Paoli Hotel Deals

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $161 total per night from Jun 28 to Jun 29
$161 total
Jun 28 - Jun 29
Total with taxes and fees
9.4/10 Exceptional! (3,887 reviews)
"Staff was friendly. Room looked like it wasn't vacuumed but not overall dirty. Room service was fast and ok. Food was VERY SALTY. Within walking distance of the Orpheum Theater."

Reviewed on Jun 20, 2026

The Madison Concourse Hotel and Governor's Club
Baymont by Wyndham Madison West/Middleton WI West

Baymont by Wyndham Madison West/Middleton WI West

2.5 out of 5
8102 Excelsior Dr Madison WI
Fully refundableReserve now, pay when you stay
$63 nightly
The price is $73 total per night from Jun 29 to Jun 30
$73 total
Jun 29 - Jun 30
Total with taxes and fees
8/10 Very Good! (1,319 reviews)
"Everything was great, except the people upstairs were so loud that I was woken up a few times. All else was really good.The rooms need some soundproof ceilings."

Reviewed on Jun 21, 2026

Baymont by Wyndham Madison West/Middleton WI West
Best Western Plus InnTowner Madison

Best Western Plus InnTowner Madison

3 out of 5
2424 University Avenue Madison WI
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $120 total per night from Jun 28 to Jun 29
$120 total
Jun 28 - Jun 29
Total with taxes and fees
9.2/10 Wonderful! (1,008 reviews)
"We enjoyed the hot tub and pool area, nice shower in the bathroom, good TV and comfy beds, and a nice breakfast setup. The staff and guests were all friendly. We would stay again."

Reviewed on Jun 20, 2026

Best Western Plus InnTowner Madison
See all 346 properties in Paoli
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 Paoli Vacation Packages

Paoli Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Dane County Regional Airport (MSN)

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Frequently asked questions

How much does a Paoli vacation package cost?
You'll find cheap prices from $519 on Expedia for your Paoli escape. However, a range of factors like the season, length of stay and your choice of hotel will influence how much your vacation to Paoli costs.
What are the cheapest months to go to Paoli?
If you're hoping to snag a cheap Paoli vacation package, consider planning a trip in November, December and January. You'll usually find lower rates on hotels and flights during these quieter months — ideal for travelers wishing to save money.
How many days is enough for Paoli?
Generally, a handful of days is enough to go to the major sights during your Paoli vacation. However, if you want to have time to kick back or take day trips, consider extending your itinerary.
How to find the best Paoli package deals?
Use Expedia's filter tool to find some terrific Paoli package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Paoli package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Paoli vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking accommodations and flights individually. Better still, you can customize your Paoli escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Paoli?
If you have your Paoli vacation dates locked in, book as early as you can to bag some fantastic deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for quick escapes.
Does Expedia offer Book Now, Pay Later Paoli vacation packages?
If you're like us, you love traveling the world but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Paoli break across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.