Search Deals onHillside Vacation Packages
Hillside Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Price was $562, price is now $369 per person
$369
per person
Nov 23 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
M
Reviewed on Sep 21, 2026
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $1,635, price is now $981 per person
$981
per person
Nov 23 - Nov 27
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.
Always great service and hospitality here. Rooms are spotless and attended to multiple times daily.
Reviewed on Sep 20, 2026
Chicago Lake Shore Hotel
Save 100% on your flight
Price was $622, price is now $389 per person
$389
per person
Nov 26 - Dec 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the overall value in our reviews. Popular attractions Soldier Field and Grant Park are located nearby.
The stairs were steep and are difficult for seniors. The air conditioning was really cool.
Reviewed on Sep 19, 2026
Level Chicago Fulton Market
Save 100% on your flight
Price was $809, price is now $527 per person
$527
per person
Dec 3 - Dec 7
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.
Amazing place to stay in Chicago!
Reviewed on Sep 18, 2026
Eaglewood Resort and Spa
Save 100% on your flight
Price was $736, price is now $487 per person
$487
per person
Nov 21 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa resort in Itasca. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodfield Mall and Bloomingdale Golf Club are located nearby.
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
Save 100% on your flight
Price was $712, price is now $480 per person
$480
per person
Nov 21 - Nov 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Allstate Arena and Rosemont Theatre are located nearby.
hotel is very dated. it’s clean & convenient to the conference center & some restaurants but very dated. Staff was great. Hotel was certainly clean.
Reviewed on Sep 20, 2026
Hotel Riu Plaza Chicago
Price was $665, price is now $450 per person
$450
per person
Nov 23 - Nov 27
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.
Only the wall outlet near the beds didn't work ...just that...everything was great !! Excelent hotel
Reviewed on Sep 21, 2026
Pendry Chicago
Save 100% on your flight
Price was $1,185, price is now $805 per person
$805
per person
Oct 24 - Oct 27
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.
Hillside Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Hillside Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Sat, Oct 17 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$158 Roundtrip, found 4 hours ago
$158
Roundtrip
found 4 hours ago
Wed, Nov 4 - Mon, Nov 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$220 Roundtrip, found 1 day ago
$220
Roundtrip
found 1 day ago
Tue, Oct 13 - Wed, Oct 21
LAX
Los Angeles Intl.
MDW
Midway Intl.
$241 Roundtrip, found 8 hours ago
$241
Roundtrip
found 8 hours ago
Fri, Nov 13 - Mon, Nov 30
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,063 Roundtrip, found 5 hours ago
$1,063
Roundtrip
found 5 hours ago
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