Paoli Vacations from $370

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The Latest Paoli Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 13 - Jan 17

    Hotel Saint Clair- Magnificent Mile + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.6/10 - Excellent (2,373 reviews)
    "Receptionist was polite, professional, and efficient. Staff was polite and friendly. Location is quite convenient. In the heart of Chicago. Price was reasonable."
    Reviewed November 5, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $565
    $370
    per traveler
    found 1 day ago
    Hotel Saint Clair- Magnificent Mile
  • Dec 18 - Dec 22

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.6/10 - Excellent (1,875 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $1,052
    $572
    per traveler
    found 1 day ago
    Sheraton Grand Chicago Riverwalk
  • Jan 7 - Jan 13

    THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel + Flight

    Downtown Chicago
    6 nights
    4.0 star property
    8.6/10 - Excellent (1,003 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $718
    $415
    per traveler
    found 1 day ago
    THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
  • Jan 13 - Jan 17

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (5,647 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $686
    $446
    per traveler
    found 1 day ago
    Hotel Riu Plaza Chicago
  • Dec 16 - Dec 19

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,162 reviews)
    "Beautiful rooms and service."
    Reviewed November 5, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $617
    $415
    per traveler
    found 1 day ago
    Pendry Chicago

Paoli Hotel Deals

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.

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.

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