Search Deals onCountryside Vacation Packages
Countryside 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 $754, price is now $496 per person
$496
per person
Oct 23 - Oct 25
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.
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $1,706, price is now $1,144 per person
$1,144
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Albuquerque (ABQ) 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.
The Peninsula Chicago
Save 100% on your flight
Price was $4,335, price is now $2,925 per person
$2,925
per person
Nov 3 - Nov 10
found 23 hours 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.
The service and the staff iare incredible, do professional!!
So many details!
My husband and I were so happy!!
Reviewed on Aug 25, 2026
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,907, price is now $1,301 per person
$1,301
per person
Oct 2 - Oct 6
found 1 day 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.
Love the place
Reviewed on Aug 30, 2026
The Langham, Chicago
Save 100% on your flight
Price was $1,716, price is now $1,193 per person
$1,193
per person
Nov 16 - Nov 20
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.
Swissotel - Chicago
Price was $1,226, price is now $870 per person
$870
per person
Nov 6 - Nov 9
found 1 day 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.
Beautiful view
Reviewed on Aug 30, 2026
LondonHouse Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $1,849, price is now $1,320 per person
$1,320
per person
Nov 3 - Nov 8
found 6 hours ago
Roundtrip flight included
Albuquerque (ABQ) 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 clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The Westin Chicago Lombard
Save 100% on your flight
Price was $1,009, price is now $728 per person
$728
per person
Nov 3 - Nov 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Lombard. Enjoy 2 restaurants, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Oakbrook Center Mall and Yorktown Shopping Center are located nearby.
Countryside Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Countryside 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.
$138 Roundtrip, found 1 hour ago
$138
Roundtrip
found 1 hour ago
Tue, Sep 22 - Tue, Sep 29
LAX
Los Angeles Intl.
MDW
Midway Intl.
$241 Roundtrip, found 3 hours ago
$241
Roundtrip
found 3 hours ago
Wed, Sep 2 - Wed, Sep 16
LAX
Los Angeles Intl.
RFD
Greater Rockford
$300 Roundtrip, found 3 days ago
$300
Roundtrip
found 3 days ago
Sat, Sep 5 - Wed, Sep 16
PEK
Capital Intl.
ORD
O'Hare Intl.
$1,184 Roundtrip, just found
$1,184
Roundtrip
just found
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