Paoli Vacations from $543

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.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $886, price is now $543 per person
$543
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,137 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!

Reviewed on May 5, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,236, price is now $728 per person
$728
per person
Jul 24 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,991 reviews)
It was a good hotel, but the room service lacked some necessary items including toothbrushes.

Reviewed on May 6, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,247, price is now $736 per person
$736
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (462 reviews)
The rooms were very clean!

Reviewed on May 4, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $890, price is now $551 per person
$551
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,293 reviews)
Having stayed in the lovely Swissotel Bosphorus/Istanbul, I was hesitant to compare Swissotel experience & hope Chicago would be as good. No. Not even close. The elevated Swissotel brand is not represented here well in this building at all. The valet is $87! Self park is $70 and the self park area doesn’t even have an elevator up to the lobby, you have to walk through a dark, confusing, and claustrophobic garage to stairs then to elevator. Staff were tactful & kind, it’s just the building is old, needs renovation, & the room air is stuffy. A positive bright light was the stunning view from the gym and the lobby ambience & smell.

Reviewed on May 6, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,531, price is now $1,007 per person
$1,007
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (973 reviews)
Rooms were cleaned I liked how secure the hotel was.

Reviewed on Apr 29, 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
$139 nightly
The price is $161 total per night from May 24 to May 25
$161 total
May 24 - May 25
Total with taxes and fees
9.4/10 Exceptional! (3,722 reviews)
The staff are knowledgeable and friendly

Reviewed on May 5, 2026

The Madison Concourse Hotel and Governor's Club
DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East

4 out of 5
4402 E Washington Ave Madison WI
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $113 total per night from May 17 to May 18
$113 total
May 17 - May 18
Total with taxes and fees
9.4/10 Exceptional! (1,015 reviews)
Great staff

Reviewed on May 6, 2026

DoubleTree by Hilton Madison East
Tru by Hilton Madison West, WI

Tru by Hilton Madison West, WI

2.5 out of 5
8102 Watts Rd. Madison WI
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $92 total per night from May 13 to May 14
$92 total
May 13 - May 14
Total with taxes and fees
9.4/10 Exceptional! (1,005 reviews)
Decent breakfast for a hotel. Very clean rooms.

Reviewed on May 4, 2026

Tru by Hilton Madison West, WI
See all 338 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 $543 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.