A waterfront building with a sign reading "Water Street."

Naperville Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Your Naperville Vacation

When you organize a vacation package to Naperville, you can relax and enjoy your break knowing that all your travel plans are under control. Discover the many charms of this city while based in a neighborhood like Clarendon Hills, which is great for golfing. Fill your free time with visits to Riverwalk, Promenade Bolingbrook and Bolingbrook Golf Club, some of the top attractions you should see during a trip to Naperville. Expedia can help you escape your daily routine. Tailor your vacation to Naperville to suit your travel style, whatever that may be!

Top Naperville vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Dec 20 - Dec 23

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.6/10 - Excellent (1,887 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $1,118
    CA $819
    per traveller
    found 1 day ago
    Sheraton Grand Chicago Riverwalk
  • Dec 19 - Dec 25

    The Emily Hotel + Flight

    Downtown Chicago
    6 nights
    4.0 star property
    9.2/10 - Wonderful (1,360 reviews)
    "Great location in the West Loop. The rooms are big and the beds are comfy. We’ve stayed there three times. The outdoor theatre shows great films and has an outdoor bar. Coffee shop is in the lobby. There’s not really a fun bar, but lots of places to have cocktails in the neighborhood. A lobby fireplace would be a nice addition in the lobby for cold Chicago nights."
    Reviewed November 13, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YYZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $1,734
    CA $1,159
    per traveller
    found 1 day ago
    The Emily Hotel
  • Dec 28 - Jan 2

    Park Hyatt Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.6/10 - Exceptional (1,000 reviews)
    "This place was amazing and the hotel staff was extremely helpful"
    Reviewed November 10, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YYZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $3,057
    CA $2,112
    per traveller
    found 8 hours ago
    Park Hyatt Chicago
  • Dec 28 - Jan 2

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    5 nights
    5.0 star property
    9.6/10 - Exceptional (2,075 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YYZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $3,161
    CA $2,208
    per traveller
    found 8 hours ago
    Trump International Hotel & Tower Chicago
  • Jan 24 - Jan 26

    Level Chicago - River North + Flight

    Downtown Chicago
    2 nights
    4.0 star property
    9.2/10 - Wonderful (1,172 reviews)
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop MDW - YUL • 1 stop
    CA $1,217
    CA $920
    per traveller
    found 1 day ago
    Level Chicago - River North

Discover the most popular places to visit in Naperville

What to do in Naperville

Naperville 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 Naperville vacation package cost?

Offering great value package deals from CA $819 on Expedia, you'll be pleasantly surprised at how much a vacation to Naperville costs! Our packages make travel planning easier and your savings go further.

What are the cheapest months to go to Naperville?

If you're hoping to score a cheap Naperville vacation package, consider visiting in December, January and February. You'll usually find better prices on hotels and airfares during these months — ideal for travellers wishing to save money.

How many days is enough for Naperville?

The ideal length of your Naperville vacation depends on what you'd like to see. Generally, a few days to a week will give you time to check out all the leading attractions and explore some hidden spots along the way.

Is it worth booking a vacation package to Naperville?

Popular for its golfing, walking trails and history, a Naperville vacation is a hit with all kinds of travellers. Be sure to visit key sights like Riverwalk and Riverwalk Park, and consider renting a car for day trips to discover even more.

How to find the best Naperville package deals?

Bagging a cheap Naperville package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can tailor your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most economical Naperville package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are typically lower.

Is it cheaper to book a Naperville vacation as a package?

Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component separately. And you'll still get the flexibility to create a personalized Naperville vacation by choosing your preferred accommodation type, airline and car class.

When to book a vacation package to Naperville?

Enjoy incredible discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Naperville trip.

How to plan a trip to Naperville?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Naperville.
  2. Figure out your budget: Make sure you have enough money to cover everything from food and transportation to flights and experiences. Your accommodations will likely be the biggest expense during your trip to Naperville.
  3. Decide how long to go for: Now that you're up to speed on Naperville, you can work out the ideal length of your break. Pull together a rough itinerary and give yourself enough time to cover everything you want to do.
  4. Combine your accommodations and airfare: After you've nailed down your travel dates and duration, book the perfect Naperville vacation package for you.

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