Woodford Vacations from $187

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Your Woodford Vacation

When you book a Woodford vacation package, you can kick back and enjoy your escape to the fullest. Discover the best parts of this unique city knowing that everything has been looked after before you go. Like some inspiration on what to do or see first during your trip to Woodford? Head for well-known attractions like Toy Train Barn. A couple of clicks is all it takes to put together a customized Woodford vacation on Expedia.

The Latest Woodford vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG

2.5 out of 5
West Lawn
Save 100% on your flight
Price was $317, price is now $187 per person
$187
per person
Feb 18 - Feb 21
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $635, price is now $355 per person
$355
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Great location, clean room and friendly staff!

Reviewed on Dec 14, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $545, price is now $321 per person
$321
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,229 reviews)
The view of our king room was beautiful. However The bathroom had blue stains on the wall, the bathroom door looked as it was kicked in, and the seating area couch by the window had stains.

Reviewed on Dec 15, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $582, price is now $347 per person
$347
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.

Reviewed on Dec 14, 2025

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $746, price is now $451 per person
$451
per person
Feb 12 - Feb 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Absolutely fantastic hotel great service, you couldn’t ask for more.

Reviewed on Dec 3, 2025

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Woodford Hotel Deals

Super 8 by Wyndham Monroe WI

Super 8 by Wyndham Monroe WI

2 out of 5
500 6th St and Hwy 69 Monroe WI
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $81 total per night from Dec 22 to Dec 23
$81 total
Dec 22 - Dec 23
Total with taxes and fees
8.8/10 Excellent! (803 reviews)
The hotel was very clean. It is an older building but very neat and tidy. The bathroom is very small and the sink area isn't even in that area. Very close to restaurants and other businesses. Employees are friendly.

Reviewed on Dec 4, 2025

Super 8 by Wyndham Monroe WI
AmericInn by Wyndham Monroe

AmericInn by Wyndham Monroe

2.5 out of 5
424 4th Ave Monroe WI
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $131 total per night from Jan 7 to Jan 8
$131 total
Jan 7 - Jan 8, 2026
Total with taxes and fees
8.6/10 Excellent! (383 reviews)
Room is very updated, nice place

Reviewed on Dec 10, 2025

AmericInn by Wyndham Monroe
Darlington Inn

Darlington Inn

2 out of 5
201 Christiensen Dr Darlington WI
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $88 total per night from Dec 16 to Dec 17
$88 total
Dec 16 - Dec 17
Total with taxes and fees
8.4/10 Very Good! (432 reviews)
We didn't eat breakfast so no opinion on that!! The room was nice and staff was fantastic. Very nice and very helpful. We came for the cheese trail and SXS riding. Very nice area and the riding was fantastic too.

Reviewed on Nov 22, 2025

Darlington Inn
See all 56 properties in Woodford
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 Woodford Vacation Packages

Woodford Essential Information

Language
English
Currency
U.S dollars
Top Sights
Yellowstone Lake State Park, Minhas Craft Brewery and Cadiz Springs State Recreation Area

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Frequently asked questions

How much does a Woodford vacation package cost?
Offering great value package deals from $187 on Expedia, you'll be thrilled with how little a vacation to Woodford costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Woodford?
You can generally find lower prices and greater availability in November, December and January. Browse our cheap Woodford vacation packages and you could land some great off-season deals.
How many days is enough for Woodford?
Typically, a handful of days is enough to tick off the top sights during your Woodford vacation. However, if you'd like to have more time to rest or take day trips, think about extending your trip.
How to find the best Woodford package deals?
Use Expedia's handy filters to help you find some terrific Woodford package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or look for Woodford package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Woodford vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and accommodations individually. Better still, you can customize your Woodford getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Woodford?
If you're considering an impromptu Woodford adventure, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land terrific deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Woodford vacation packages?
Your Woodford getaway should be a relaxing escape from your daily routine, not a source of money-related stress. So to give you more flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.