Paoli Vacations from $415

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The Latest Paoli Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A rooftop lounge with outdoor seating and a city skyline view.
    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
  • A cityscape with modern high-rise buildings, a river, and a bridge.
    Dec 20 - Dec 23

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.6/10 - Excellent (1,875 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $1,483
    $471
    per traveler
    found 1 day ago
    Sheraton Grand Chicago Riverwalk
  • The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.
    Jan 22 - Jan 25

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.4/10 - Exceptional (5,647 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $730
    $493
    per traveler
    found 1 day ago
    Hotel Riu Plaza Chicago
  • A modern living room with a grey sofa, a round coffee table with a plant, and a TV mounted on the wall.
    Dec 28 - Jan 1

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (602 reviews)
    "If you are looking to stay in a condo type setting, this may be your spot. I checked in which you need to go through a process that takes 15 minutes, (do it before) and they automatically add a $25 per night fee for their gym and roof top. This was NOT published on Hotels.com or any other site. A total rip off as this is not a spa. There was no housekeeping. Checking in took 15 minutes in which there was little to no Wifi, so I had to go do this outside (crazy?). Do the check-in before..."
    Reviewed November 4, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $931
    $631
    per traveler
    found 1 day ago
    Level Chicago Fulton Market
  • A modern living room with a sofa, chairs, a coffee table, and a TV. A large window offers a view of a cityscape and a tower.
    Dec 10 - Dec 13

    Park Hyatt Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,001 reviews)
    "Given the price point and other reviews, we came here expecting a luxury stay similar to the Waldorf Astoria, Four Seasons, and Peninsula, which are some of our favorite properties to stay at. However, everything from the service and cleanliness to the ambiance of the entrance and lobby and the amenities (other than the gym, which was excellent) is best described as an upgraded version of an average Hilton, Hyatt, or Marriott. For example, there was a hair in the bed. When we reported it, the..."
    Reviewed November 4, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - MDW • Nonstop ORD - ATL • Nonstop
    $1,826
    $1,237
    per traveler
    found 6 hours ago
    Park Hyatt Chicago

Paoli Hotel Deals

A modern hotel with a covered entrance, multiple floors, and a parking lot.

Hyatt Place Madison / Verona

Hyatt Place Madison / Verona
3.0 star property
3.3 mi from Paoli
9.4 out of 10, Exceptional, (1,001 reviews)
$116 nightly
The price is $131
Nov 22 - Nov 23
Total with taxes and fees
Hyatt Place Madison / Verona
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.
See all properties in Paoli

Frequently Asked Questions

How much does a Paoli vacation package cost?

You'll find cheap prices from $415 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.