Search Deals onAddison Vacation Packages
Addison Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Save 100% on your flight
Price was $590, price is now $389 per person
$389
per person
Jan 15 - Jan 18
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.
Four Seasons Hotel Chicago
Save 100% on your flight
Price was $1,469, price is now $894 per person
$894
per person
Dec 24 - Dec 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 in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Great place to stay in Chicago!
Reviewed on Oct 21, 2026
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,254, price is now $775 per person
$775
per person
Nov 28 - Dec 1
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.
The Peninsula Chicago
Save 100% on your flight
Price was $1,912, price is now $1,183 per person
$1,183
per person
Jan 1 - Jan 6
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 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Always an incredible hotel! Definitely one of the best in the USA
Reviewed on Oct 21, 2026
Park Hyatt Chicago
Save 100% on your flight
Price was $1,671, price is now $1,084 per person
$1,084
per person
Jan 1 - Jan 6
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 Fulton Market
Save 100% on your flight
Price was $659, price is now $433 per person
$433
per person
Jan 7 - Jan 13
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.
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $1,463, price is now $976 per person
$976
per person
Nov 28 - Dec 1
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.
Toilet paper was sub par
Reviewed on Oct 22, 2026
Level Chicago - River North
Save 100% on your flight
Price was $911, price is now $616 per person
$616
per person
Jan 7 - Jan 13
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.
Addison Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Addison 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.
Tue, Nov 17 - Thu, Nov 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$179 Roundtrip, found 3 hours ago
$179
Roundtrip
found 3 hours ago
Wed, Nov 11 - Tue, Nov 17
LAX
Los Angeles Intl.
MDW
Midway Intl.
$196 Roundtrip, just found
$196
Roundtrip
just found
Tue, Nov 17 - Thu, Nov 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$199 Roundtrip, found 3 hours ago
$199
Roundtrip
found 3 hours ago
Fri, Nov 13 - Wed, Nov 25
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,125 Roundtrip, found 2 hours ago
$1,125
Roundtrip
found 2 hours ago
Discover Other Travel Deals
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations
