Paoli Vacations from $370
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The Latest Paoli Vacation Packages
- Hotel Saint Clair- Magnificent Mile
Jan 13 - Jan 17Hotel Saint Clair- Magnificent Mile + Flight
Downtown Chicago4 nights4.0 star property8.6/10 - Excellent (2,378 reviews)"Very walkable to Michigan Avenue with chic modern designs in a vintage building. Friendly staff. Stayed for one night, very comfortable and clean room."Reviewed November 6, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop$556$370found 1 day agoper traveler - Sheraton Grand Chicago Riverwalk
Dec 10 - Dec 13Sheraton Grand Chicago Riverwalk + Flight
Downtown Chicago3 nights4.0 star property8.6/10 - Excellent (1,877 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • Nonstop ORD - ATL • Nonstop$599$378found 1 day agoper traveler - Pendry Chicago
Dec 10 - Dec 13Pendry Chicago + Flight
Downtown Chicago3 nights4.5 star property9.2/10 - Wonderful (1,162 reviews)"Beautiful rooms and service."Reviewed November 5, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • Nonstop ORD - ATL • Nonstop$824$521found 1 day agoper traveler - THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Jan 13 - Jan 17THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel + Flight
Downtown Chicago4 nights4.0 star property8.6/10 - Excellent (1,006 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop$590$376found 1 day agoper traveler - Level Chicago Fulton Market
Dec 24 - Dec 29Level Chicago Fulton Market + Flight
Downtown Chicago5 nights4.0 star property9.2/10 - Wonderful (603 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop$858$558found 1 day agoper traveler
Paoli Hotel Deals
"No continental breakfast and coffee was not filled in the morning for guests. Otherwise I would have given 5 stars."
Springhill Suites By Marriott Madison Fitchburg
Springhill Suites By Marriott Madison Fitchburg"Great location and clean!"
Staybridge Suites Madison - Fitchburg by IHG
Staybridge Suites Madison - Fitchburg by IHG"Joseph (General Manager) & Lucky were amazing. Their customers service went above and beyond."
Sleep Inn & Suites Oregon - Madison
Sleep Inn & Suites Oregon - Madison"I was just looking for a clean well kept hotel for a wedding I was attending and I found it in this hotel. Great clean typical hotel room with comfortable beds. Pool looked nice and breakfast was good! Highly recommended!"
Holiday Inn Express Hotel & Suites Madison-Verona by IHG
Holiday Inn Express Hotel & Suites Madison-Verona by IHG
Country Inn & Suites by Radisson, Madison Southwest, WI
Country Inn & Suites by Radisson, Madison Southwest, WI"the staff are helpfuland have fitness gym."
Fairfield Inn & Suites by Marriott Madison Verona
Fairfield Inn & Suites by Marriott Madison Verona
AmericInn by Wyndham Madison West
AmericInn by Wyndham Madison West"The room was very comfortable. The pool and whirlpool were both open. And the breakfast was the best I’ve had in a long time."
Frequently Asked Questions
How much does a Paoli vacation package cost?
You'll find cheap prices from $370 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.