Paoli Vacations from $758

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Paoli vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,209, price is now $758 per person
$758
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)
We enjoyed the roof top bar and the glass floor experience in the roof top bar Room was clean and breakfast changed daily In a good area for attractions and transport

Reviewed on Aug 5, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was $3,387, price is now $1,838 per person
$1,838
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,041 reviews)

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $4,667, price is now $2,726 per person
$2,726
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Late on room service. Forgot items requested, making room service even later. Tv was not plugged in correctly and wasted my time. If i pay this much for a room for 2 nights I really expect these simple things to work the first time and me not have to waste my time trying to figure out why the tv isnt working. Idk i think some of the staff is a little confused or lazy im not sure. Beautiful hotel and beautiful room with a great view. Also the wings from room service could be SOO muchh better. Thanks for taking all my money tho!

Reviewed on Aug 4, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,430, price is now $1,466 per person
$1,466
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (509 reviews)

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 $1,265, price is now $784 per person
$784
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,606 reviews)
Our stay was amazing with a beautiful view.

Reviewed on Aug 5, 2026

Don't see what you're looking for?
See all available trips from Columbus to Paoli
View all trips

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
$140 nightly
The price is $162 total per night from Aug 9 to Aug 10
$162 total
Aug 9 - Aug 10
Total with taxes and fees
9.4/10 Exceptional! (4,059 reviews)
"Check in was easy, no pool. Parking garage got very low however my 2011 gmc sierra 1500 fit."

Reviewed on Aug 5, 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
$57 nightly
The price is $66 total per night from Aug 23 to Aug 24
$66 total
Aug 23 - Aug 24
Total with taxes and fees
8/10 Very Good! (1,407 reviews)
"bar was closed, left before breakfast served"

Reviewed on Aug 5, 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
$126 nightly
The price is $146 total per night from Aug 30 to Aug 31
$146 total
Aug 30 - Aug 31
Total with taxes and fees
9.2/10 Wonderful! (1,009 reviews)
"Great breakfast buffet"

Reviewed on Aug 4, 2026

Best Western Plus InnTowner Madison
See all 347 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)

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Paoli vacation package cost?
You'll find cheap prices from $758 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.

Explore a world of travel with Expedia

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