Search Deals on
Hillside Vacation Packages

Build your package with 2 more options

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 $1,495, price is now $800 per person
$800
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 $1,820, 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)
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.
En publicidad ofrecen uso de piscina en un entorno agradable familiar y fue lo contrario parejas en actos lasivos dentro de piscina y ninguna persona de servicio atentos a lo que pasa totalmente desagradable.

Reviewed on Aug 24, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $968, price is now $605 per person
$605
per person
Nov 13 - Nov 15
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.

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 20 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.
I had a wonderful stay! The breakfast was absolutely outstanding. The whole space was clean and well maintained. Staff were very friendly and helpful. I really appreciated the flexibility of checking my luggage before and after check-in/out. I will definitely be back!

Reviewed on Aug 24, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Save 100% on your flight
Price was $833, price is now $543 per person
$543
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $1,904, price is now $1,243 per person
$1,243
per person
Oct 27 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions United Center and Chicago Riverwalk are located nearby.

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Save 100% on your flight
Price was $1,210, price is now $802 per person
$802
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, 2 bars/lounges, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

Hillside Vacation Packages 3-4 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 $747, price is now $484 per person
$484
per person
Oct 4 - Oct 7
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 $1,139, price is now $672 per person
$672
per person
Oct 28 - Nov 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 $1,073, 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)
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,179, price is now $750 per person
$750
per person
Oct 28 - Nov 1
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.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,297, price is now $715 per person
$715
per person
Oct 28 - Nov 3
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 $1,495, price is now $800 per person
$800
per person
Oct 28 - Nov 3
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)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,910, price is now $1,077 per person
$1,077
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 15 - Tue, Oct 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$148 Roundtrip, just found
$148
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Oct 15 from Los Angeles Intl. to O'Hare Intl., returning Tue, Oct 20, priced at $148 just found
Southwest Airlines
Sat, Sep 26 - Wed, Sep 30
LAX
Los Angeles Intl.
MDW
Midway Intl.
$210 Roundtrip, found 1 day ago
$210
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Sep 26 from Los Angeles Intl. to Midway Intl., returning Wed, Sep 30, priced at $210 found 1 day ago
American Airlines
Wed, Sep 2 - Tue, Sep 8
LAX
Los Angeles Intl.
RFD
Greater Rockford
$429 Roundtrip, found 1 day ago
$429
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Sep 2 from Los Angeles Intl. to Greater Rockford, returning Tue, Sep 8, priced at $429 found 1 day 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