Search Deals onCountryside Vacation Packages
Countryside Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Le Méridien Essex Chicago
Price was $493, price is now $338 per person
$338
per person
Jan 15 - Jan 19
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, room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.
I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything.
Reviewed on Nov 3, 2026

The Emily Hotel
Save 100% on your flight
Price was $830, price is now $507 per person
$507
per person
Dec 24 - Dec 29
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.
Staff was friendly and the room was clean
Reviewed on Nov 3, 2026

Hotel Riu Plaza Chicago
Price was $1,149, price is now $707 per person
$707
per person
Dec 30 - Jan 4
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.
We thoroughly enjoyed our stay at the Riu Hotel. The location was fantastic. You could go shopping or walk to the lakefront in 5 minutes. The rooms were modern and immaculate. The breakfast was included in our reservation and was great. We were also able to enjoy the rooftop bar with a heater. We would definitely recommend staying here
Reviewed on Nov 4, 2026

Level Chicago Fulton Market
Price was $639, price is now $403 per person
$403
per person
Jan 5 - Jan 10
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.

Pendry Chicago
Price was $609, price is now $400 per person
$400
per person
Dec 16 - Dec 19
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.

Level Chicago – Old Town
Save 100% on your flight
Price was $718, price is now $480 per person
$480
per person
Jan 25 - Jan 28
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.
Estuvo muy increíble, fue una experiencia maravillosa.Es un lugar precioso me encantó
Reviewed on Nov 1, 2026

Hotel Felix River North/Magnificent Mile
Price was $630, price is now $437 per person
$437
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
very loud. at night = motorcycles outside all night. inside, drunk people screaming and pounding doors = was awakened two days in a row btw 330 and 5 am by loud guests. to their credit, the front desk called security. the smell of marijuana was not uncommon in the hallways. it was a good location for the event we were attending but this is second tier hotel w/ very well meaning staff.
Reviewed on Nov 3, 2026

The Talbott, Autograph Collection
Price was $757, price is now $533 per person
$533
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury 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 Michigan Avenue and Chicago Riverwalk 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
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Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Fri, Dec 4 - Wed, Dec 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$176 Roundtrip, found 9 hours ago
$176
Roundtrip
found 9 hours ago

Wed, Dec 2 - Fri, Dec 4
LAX
Los Angeles Intl.
MDW
Midway Intl.
$238 Roundtrip, found 12 hours ago
$238
Roundtrip
found 12 hours ago
Mon, Nov 9 - Mon, Feb 1
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,141 Roundtrip, just found
$1,141
Roundtrip
just found
Sun, Nov 8 - Mon, Feb 1
SHA
Hongqiao Intl.
ORD
O'Hare Intl.
$1,570 Roundtrip, found 1 day ago
$1,570
Roundtrip
found 1 day ago
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