Arena Vacations from $474
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The Latest Arena Vacation Packages
- AmericInn & Suites By Wyndham Baraboo Event Center
Oct 16 - Oct 21AmericInn & Suites By Wyndham Baraboo Event Center + Flight
Baraboo5 nights3.0 star property7.8/10 - Good (1,011 reviews)Roundtrip • Chicago (CHI) - Madison (MSN)ORD - MSN • Nonstop MSN - ORD • Nonstop$573$474found 8 hours agoper traveler - The Edgewater
Sep 25 - Sep 28The Edgewater + Flight
Downtown Madison3 nights4.5 star property9.2/10 - Wonderful (1,009 reviews)Roundtrip • Chicago (ORD) - Madison (MSN)ORD - MSN • Nonstop MSN - ORD • Nonstop$916$729found 15 hours agoper traveler - Wingate by Wyndham Wisconsin Dells Waterpark
Oct 16 - Oct 21Wingate by Wyndham Wisconsin Dells Waterpark + Flight
Baraboo5 nights3.0 star property8.8/10 - Excellent (1,002 reviews)"Breakfast terrible. I don't recommend"Reviewed August 4, 2026Roundtrip • Chicago (CHI) - Madison (MSN)ORD - MSN • Nonstop MSN - ORD • Nonstop$588$484found 8 hours agoper traveler - Fairfield Inn & Suites by Marriott Madison East
Sep 30 - Oct 4Fairfield Inn & Suites by Marriott Madison East + Flight
Madison4 nights3.0 star property9.2/10 - Wonderful (1,004 reviews)"Very convenient and close to everything. An excellent place to stay."Reviewed July 31, 2026Roundtrip • Chicago (CHI) - Madison (MSN)ORD - MSN • Nonstop MSN - ORD • Nonstop$1,045$867found 14 hours agoper traveler - The Madison Concourse Hotel and Governor's Club
Sep 30 - Oct 4The Madison Concourse Hotel and Governor's Club + Flight
Downtown Madison4 nights3.5 star property9.4/10 - Exceptional (4,059 reviews)"Check in was easy, no pool. Parking garage got very low however my 2011 gmc sierra 1500 fit."Reviewed August 5, 2026Roundtrip • Chicago (CHI) - Madison (MSN)ORD - MSN • Nonstop MSN - ORD • Nonstop$1,583$1,335found 13 hours agoper traveler
Arena Hotel Deals
"Fabulous hot breakfast. Brand new showers in all units"
Homewood Suites by Hilton Madison West
Homewood Suites by Hilton Madison West"Just a really nice place. Will be back"
Holiday Inn Express & Suites Madison West - Middleton by IHG
Holiday Inn Express & Suites Madison West - Middleton by IHG
Residence Inn by Marriott Madison West/Middleton
Residence Inn by Marriott Madison West/Middleton"The staff at this property is the best"
Courtyard by Marriott Madison West Middleton
Courtyard by Marriott Madison West Middleton"The bistro pricing posted on signage did not match the pricing in the menus. I was informed the menus needed to be updated but the lower pricing was not honoured."
Fairfield Inn & Suites by Marriott Madison West/Middleton
Fairfield Inn & Suites by Marriott Madison West/Middleton
TownePlace Suites by Marriott Madison West/Middleton
TownePlace Suites by Marriott Madison West/Middleton"loved it!"
Frequently Asked Questions
How much does an Arena vacation package cost?
You can snap up a vacation package to this destination from $474 on Expedia. But how much your vacation to Arena costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Arena?
You can usually find lower prices and greater availability in December, January and February. Check out our cheap Arena vacation packages and you could land some great off-season discounts.
How many days is enough for Arena?
With a well-organized itinerary, you can easily visit the main Arena attractions in a few days. But if you prefer to discover hidden gems or take day trips, think about booking your Arena vacation for longer.
How to find the best Arena package deals?
Use Expedia's handy filters to help you find some fabulous Arena package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or browse for Arena package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book an Arena vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually snag a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Arena vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Arena?
Enjoy incredible discounts by reserving your flights in advance with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Arena break.
Does Expedia offer Book Now, Pay Later Arena vacation packages?
If you're like us, you love jet-setting around the world but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Arena break across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you see them.