Deals on vacations and trips to Paoli

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Paoli flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Delta Hotels by Marriott Chicago Willowbrook

Delta Hotels by Marriott Chicago Willowbrook

3 out of 5
Price was $503, price is now $372 per person
$372
per person
Feb 19 - Feb 24
found 6 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a grocery/convenience store, and a computer station are also offered.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was $1,516, price is now $1,058 per person
$1,058
per person
Feb 19 - Feb 24
found 6 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $847, price is now $602 per person
$602
per person
Mar 12 - Mar 17
found 13 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and a coffee shop are also provided.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $793, price is now $582 per person
$582
per person
Mar 12 - Mar 17
found 13 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a coffee shop, and a snack bar/deli are also offered.
Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Price was $1,207, price is now $890 per person
$890
per person
Feb 19 - Feb 24
found 6 hours ago
Roundtrip flight included
San Juan (SJU) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. A coffee shop, express check-out, and dry cleaning are also on offer.

Top Paoli hotels 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
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $161 total per night
$161 total
Dec 28 - Dec 29
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. There's a gym on site, and a 24-hour front desk and a coffee shop are also provided.
Pool
Hot Tub
DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East

4 out of 5
4402 E Washington Ave Madison WI
Free Cancellation
Reserve now, pay when you stay
$106 nightly
The price is $122 total per night
$122 total
Dec 28 - Dec 29
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Pet friendly
Hampton Inn & Suites Madison-West

Hampton Inn & Suites Madison-West

2.5 out of 5
483 Commerce Dr Madison WI
Free Cancellation
Reserve now, pay when you stay
$71 nightly
The price is $82 total per night
$82 total
Jan 9 - Jan 10, 2026
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
Pool
Hot Tub
Tru by Hilton Madison West, WI

Tru by Hilton Madison West, WI

2.5 out of 5
8102 Watts Rd. Madison WI
Free Cancellation
Reserve now, pay when you stay
$66 nightly
The price is $76 total per night
$76 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's a 24-hour gym on site, and a 24-hour front desk and a terrace are also provided.
Breakfast included
Pet friendly
The Edgewater

The Edgewater

4.5 out of 5
1001 Wisconsin Place Madison WI
Free Cancellation
Reserve now, pay when you stay
$221 nightly
The price is $255 total per night
$255 total
Dec 27 - Dec 28
Total with taxes and fees
A full-service spa, a hot tub, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, express check-in, and free airport shuttle. Unwind with a drink at one of the 4 bars/lounges and enjoy perks like a free area shuttle.
Hot Tub
Spa
Hampton Inn & Suites Madison / Downtown

Hampton Inn & Suites Madison / Downtown

2.5 out of 5
440 West Johnson Street Madison WI
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $113 total per night
$113 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and free buffet breakfast each morning.
Pool
Breakfast included
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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 are vacation packages to Paoli?
Travelocity has flight and hotel vacation packages starting from just $372. With such huge savings, you'll be saying hello to Paoli before too long.
Where can I get the best vacation package deals for Paoli?
You can lock in unbeatable Paoli package deals with Travelocity. Pick from as many as 400 air carriers and 1,000,000 worldwide properties and turn those vacation daydreams into a reality.
Why should I purchase my Paoli vacation bundle via Travelocity?
You'll not only enjoy great savings, but you can also access our 24/7 support, quality service and a Price Match Guarantee. Roam across the globe, discover hidden gems and make lifelong memories — we'll take care of the little details.
Will I save money on my Paoli car rental if I combine it with a hotel or flight?
You most certainly can — and booking one of our Paoli vacation packages is an excellent way to go about this. Bundle any combination of a car, flight, hotel and experience and score serious discounts. The more you bundle, the more you'll save. There are so many landmarks around Paoli to add to your itinerary, including Wrigley Field (120 mi from Paoli). Nothing tops discovering thrilling places like this with the freedom of your own rental car.

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