Naperville Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination
Price was CA $1,084, price is now CA $784 per person
CA $784
per person
Sep 11 - Sep 14
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.6/10 Excellent! (1,024 reviews)
Clean large room. Friendly helpful staff. Garage parking with covered bridge to hotel and casino. Highly recommend.
Reviewed on Jun 25, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $3,635, price is now CA $2,437 per person
CA $2,437
per person
Sep 12 - Sep 18
found 22 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,544, price is now CA $1,096 per person
CA $1,096
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Clean rooms and comfortable beds but the windows were a little thin that you could hear everything outside.
Reviewed on Jun 27, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,991, price is now CA $2,125 per person
CA $2,125
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
Upscale amazing stay in trendy neighborhood in Chcago. Walking distance to coffee shops, great restaurants. The amenities were beyond what I expected/ great lap pool, hot tubs, sauna steam room and amazing gym with enough equipment to do a full strength training workout. We will stay here again!
Reviewed on Jun 25, 2026
Omni Chicago Hotel
Downtown Chicago
Price was CA $1,180, price is now CA $865 per person
CA $865
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,813 reviews)
The staff were very helpful and kind, room clean and a beautiful view. Hotel kept up very well. Our air conditioning worked great on the 23rd floor. Check out, bags held and valet parking plus retrieval very quick and excellent service.
Reviewed on Jun 27, 2026
Naperville Hotel Deals
DoubleTree by Hilton Lisle Naperville
3003 Corporate West Dr Naperville IL
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from Jul 6 to Jul 7
CA $127
CA $141 total
Jul 6 - Jul 7
includes taxes & fees
7.8/10 Good! (1,341 reviews)
"OMG, the 1980s called and wants their furniture back. This place had an ARMOIRE with POCKET DOORS!! The sofa was also about a hundred years old. Pretty clear they haven’t spent a cent on guest room furniture since the Reagan administration. Props to the bed tho, it was sort of comfortable"
Reviewed on Jun 25, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $181 per night from Jun 29 to Jun 30
CA $181
CA $206 total
Jun 29 - Jun 30
includes taxes & fees
8.8/10 Excellent! (2,734 reviews)
"ALWAYS ask for Gina (I believe it is); she is one of the front desk managers. Extremely helpful."
Reviewed on Jun 27, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $361 per night from Jul 4 to Jul 5
CA $361
CA $423 total
Jul 4 - Jul 5
includes taxes & fees
8.4/10 Very good! (2,318 reviews)
"Clean room, staff were very helpful and very friendly. Restaurants and bar were on point. Great experience! Thanks Hilton Chicago O’Hare Airport!"
Reviewed on Jun 25, 2026
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.
Stay near popular Naperville attractions
What to do in Naperville
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $56
per adult
94% of travellers recommend
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
