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Hillside Vacation Packages

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Hillside Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Save 100% on your flight
Price was $582, price is now $386 per person
$386
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Joliet. Enjoy free WiFi, 3 restaurants, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicagoland Speedway and Route 66 Raceway are located nearby.

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,493, price is now $799 per person
$799
per person
Oct 28 - Nov 3
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.

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,217, price is now $685 per person
$685
per person
Oct 2 - Oct 6
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. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
They need to figure out a better parking garage system!!!!

Reviewed on Aug 23, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,274, price is now $825 per person
$825
per person
Nov 13 - Nov 17
found 12 hours ago
Roundtrip flight included
Albuquerque (ABQ) 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 new LEED hotel. Staff were exceptional. Unique part of the room was that you had to place your room key in reader inside your room in order to activate electricity ( room Lights,TV, etc.). I suggest they make visitors aware when they check in. Liked the safety features with the elevator too.

Reviewed on Aug 24, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $2,019, price is now $1,351 per person
$1,351
per person
Oct 14 - Oct 19
found 13 hours ago
Roundtrip flight included
Albuquerque (ABQ) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Rooms are extremely cold. Glass/ mirrors & table dirty with fingerprints & crumbs still on table. Shower leaked water all over floor. Toilet had hair on it. Not informed about hidden $30 feet a day. Did not sleep comfortably during stay due to room temperature

Reviewed on Aug 23, 2026

Ohio House Motel

Ohio House Motel

3 out of 5
Save 100% on your flight
Price was $891, price is now $597 per person
$597
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this motel in Chicago. Enjoy free WiFi, breakfast (surcharge), and parking (surcharge). Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Great staff who helped us checkin after a long drive. Although it looks so-so from the street, the rooms are great. We would come back here again.

Reviewed on Aug 24, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,030, price is now $704 per person
$704
per person
Nov 2 - Nov 5
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 rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Staff was EXCELLENT

Reviewed on Aug 23, 2026

Villa Christina

Villa Christina

3 out of 5
Save 100% on your flight
Price was $984, price is now $673 per person
$673
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this guesthouse in Chicago. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Griffin Museum of Science and Industry and Rate Field are located nearby.
Property was maintained very well, very clean with some artful style. Staff reaponsed quickly fie any needs or inquiry. Feels like a home. Community is safe and neighbors are nice. Street parking is reletively easy.

Reviewed on Aug 4, 2026

Hillside Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,073, price is now $673 per person
$673
per person
Oct 28 - Nov 1
found 18 hours 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 $1,217, price is now $685 per person
$685
per person
Oct 2 - Oct 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 $1,274, price is now $825 per person
$825
per person
Nov 13 - Nov 17
found 12 hours ago
Roundtrip flight included
Albuquerque (ABQ) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,764, price is now $1,153 per person
$1,153
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Hillside Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $850, price is now $500 per person
$500
per person
Oct 30 - Nov 4
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 $1,493, price is now $799 per person
$799
per person
Oct 28 - Nov 3
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 $1,242, price is now $694 per person
$694
per person
Oct 30 - Nov 4
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 $1,820, price is now $1,020 per person
$1,020
per person
Oct 27 - Nov 3
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
Thu, Oct 22 - Mon, Oct 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$118 Roundtrip, found 5 days ago
$118
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Oct 22 from Los Angeles Intl. to O'Hare Intl., returning Mon, Oct 26, priced at $118 found 5 days ago
Southwest Airlines
Sat, Sep 26 - Wed, Sep 30
LAX
Los Angeles Intl.
MDW
Midway Intl.
$210 Roundtrip, found 16 hours ago
$210
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Sat, Sep 26 from Los Angeles Intl. to Midway Intl., returning Wed, Sep 30, priced at $210 found 16 hours ago
American Airlines
Wed, Sep 2 - Tue, Sep 8
LAX
Los Angeles Intl.
RFD
Greater Rockford
$429 Roundtrip, found 21 hours ago
$429
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Wed, Sep 2 from Los Angeles Intl. to Greater Rockford, returning Tue, Sep 8, priced at $429 found 21 hours ago
Asiana Airlines
Fri, Nov 13 - Mon, Nov 30
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,082 Roundtrip, found 3 days ago
$1,082
Roundtrip
found 3 days ago
Select Asiana Airlines flight, departing Fri, Nov 13 from Pudong Intl. to O'Hare Intl., returning Mon, Nov 30, priced at $1,082 found 3 days ago