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Naperville Vacation Packages

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Naperville Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $884, price is now $549 per person
$549
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,515, price is now $917 per person
$917
per person
Sep 30 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
this is no a hotel and the amenities are bare bones. No maid service, the TV was worthless with endless buffering to make it unwatchable, the shower head was broken, etc. On the good side, it's a great location, beautiful views, nice vibe around the property, large unit with two beds, and great gym area.

Reviewed on Jul 27, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,022, price is now $640 per person
$640
per person
Sep 2 - Sep 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Beautiful, affordable. Great stay

Reviewed on Jul 27, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Save 100% on your flight
Price was $2,796, price is now $1,825 per person
$1,825
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Level Chicago - River North

Level Chicago - River North

4 out of 5
Save 100% on your flight
Price was $1,214, price is now $834 per person
$834
per person
Sep 16 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
We had such a great stay! Only complaint was one of the blinds would not shut in one of the bedrooms, but we understood it was probably not fixable in the 2 days we were there. We were also upgraded to a better room upon arrival! Overall 10/10!

Reviewed on Jul 23, 2026

The Langham, Chicago

5 out of 5
Save 100% on your flight
Price was $3,251, price is now $2,286 per person
$2,286
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,554, price is now $1,101 per person
$1,101
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Great location !! Great hotel !! Great service

Reviewed on Jul 27, 2026

Kinzie Hotel

Kinzie Hotel

4 out of 5
Save 100% on your flight
Price was $982, price is now $697 per person
$697
per person
Sep 30 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Very clean good sized room. Friendly and helpful staff. Ideally located for the river walk and bars/restaurants

Reviewed on Jul 27, 2026

Naperville Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $884, price is now $549 per person
$549
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,010, price is now $611 per person
$611
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,343, price is now $860 per person
$860
per person
Sep 27 - Oct 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,035, price is now $672 per person
$672
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Naperville Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $989, price is now $591 per person
$591
per person
Sep 30 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,592, price is now $862 per person
$862
per person
Sep 30 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,639, price is now $946 per person
$946
per person
Sep 30 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,515, price is now $917 per person
$917
per person
Sep 30 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Tue, Sep 1 - Fri, Sep 4
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$186 Roundtrip, found 12 hours ago
$186
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Tue, Sep 1 from Los Angeles Intl. to O'Hare Intl., returning Fri, Sep 4, priced at $186 found 12 hours ago
Frontier Airlines
Thu, Aug 27 - Sat, Aug 29
LAX
Los Angeles Intl.
MDW
Midway Intl.
$240 Roundtrip, found 4 hours ago
$240
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Thu, Aug 27 from Los Angeles Intl. to Midway Intl., returning Sat, Aug 29, priced at $240 found 4 hours ago
American Airlines
Wed, Sep 2 - Tue, Sep 8
LAX
Los Angeles Intl.
RFD
Greater Rockford
$250 Roundtrip, found 3 hours ago
$250
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Wed, Sep 2 from Los Angeles Intl. to Greater Rockford, returning Tue, Sep 8, priced at $250 found 3 hours ago
Turkish Airlines
Tue, Sep 1 - Fri, Sep 18
PEK
Capital Intl.
ORD
O'Hare Intl.
$1,190 Roundtrip, found 3 hours ago
$1,190
Roundtrip
found 3 hours ago
Select Turkish Airlines flight, departing Tue, Sep 1 from Capital Intl. to O'Hare Intl., returning Fri, Sep 18, priced at $1,190 found 3 hours ago