Naperville Vacation Packages

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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.
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was CA $1,003, price is now CA $755 per person
CA $755
per person
Jun 22 - Jun 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,144 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!

Reviewed on May 5, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,495, price is now CA $1,036 per person
CA $1,036
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (973 reviews)
Very clean, many amenities

Reviewed on May 9, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,567, price is now CA $1,090 per person
CA $1,090
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (471 reviews)
The rooms were very clean!

Reviewed on May 4, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,968, price is now CA $1,453 per person
CA $1,453
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,122 reviews)
Great staff and perfect place to be in the middle of everything!

Reviewed on Apr 27, 2026

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was CA $1,123, price is now CA $834 per person
CA $834
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (2,281 reviews)
Wonderful location, staff were very helpful and room was clean. Older hotel but well maintained. Pricey but worthwhile for convenience sake.

Reviewed on May 5, 2026

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Naperville Hotel Deals

DoubleTree by Hilton Lisle Naperville

DoubleTree by Hilton Lisle Naperville

4 out of 5
3003 Corporate West Dr Naperville IL
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from May 31 to Jun 1
CA $122
CA $136 total
May 31 - Jun 1
includes taxes & fees
7.8/10 Good! (1,316 reviews)
Property in mid renovation, very outdated, halls were loud each night, tough to get hot water.

Reviewed on May 7, 2026

DoubleTree by Hilton Lisle Naperville
Best Western Naperville Inn

Best Western Naperville Inn

2.5 out of 5
1617 Naperville Wheaton Rd Naperville IL
Fully refundableReserve now, pay when you stay
The price is CA $131 per night from May 27 to May 28
CA $131
CA $146 total
May 27 - May 28
includes taxes & fees
Best Western Naperville Inn
Embassy Suites by Hilton Chicago Naperville

Embassy Suites by Hilton Chicago Naperville

3.5 out of 5
1823 Abriter Court Naperville IL
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from May 24 to May 25
CA $185
CA $206 total
May 24 - May 25
includes taxes & fees
8.4/10 Very Good! (1,165 reviews)
10/10 I will recommend!!!

Reviewed on May 8, 2026

Embassy Suites by Hilton Chicago Naperville
See all 1,510 properties in Naperville
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Naperville

Wrigley Field

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Naperville

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in Naperville

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