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Countryside Vacation Packages

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Countryside Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $595, price is now $418 per person
$418
per person
Aug 27 - Aug 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,086, price is now $710 per person
$710
per person
Sep 3 - Sep 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 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

Level Chicago – Old Town

4 out of 5
Save 100% on your flight
Price was $1,190, price is now $778 per person
$778
per person
Sep 13 - Sep 16
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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $908, price is now $597 per person
$597
per person
Aug 27 - Aug 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 breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $867, price is now $579 per person
$579
per person
Sep 3 - Sep 6
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.
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Save 100% on your flight
Price was $750, price is now $510 per person
$510
per person
Aug 27 - Aug 29
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 breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Save 100% on your flight
Price was $819, price is now $586 per person
$586
per person
Sep 4 - Sep 8
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.
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $747, price is now $536 per person
$536
per person
Aug 27 - Aug 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.

Countryside Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $867, price is now $579 per person
$579
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,086, price is now $710 per person
$710
per person
Sep 3 - Sep 6
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 $1,190, price is now $778 per person
$778
per person
Sep 13 - Sep 16
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 $1,150, price is now $757 per person
$757
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Countryside Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,043, price is now $621 per person
$621
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was $1,583, price is now $869 per person
$869
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was $2,582, price is now $1,626 per person
$1,626
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,184, price is now $751 per person
$751
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Sat, Aug 15 - Sat, Aug 29
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$202 Roundtrip, found 1 day ago
$202
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Aug 15 from Los Angeles Intl. to O'Hare Intl., returning Sat, Aug 29, priced at $202 found 1 day ago
Frontier Airlines
Sun, Aug 9 - Mon, Aug 24
LAX
Los Angeles Intl.
MDW
Midway Intl.
$252 Roundtrip, found 14 hours ago
$252
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Sun, Aug 9 from Los Angeles Intl. to Midway Intl., returning Mon, Aug 24, priced at $252 found 14 hours ago
American Airlines
Sat, Jul 18 - Sat, Jul 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$419 Roundtrip, found 2 days ago
$419
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Jul 18 from Los Angeles Intl. to Greater Rockford, returning Sat, Jul 25, priced at $419 found 2 days ago
Icelandair
Sat, Jul 4 - Sat, Jul 18
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$728 Roundtrip, found 3 days ago
$728
Roundtrip
found 3 days ago
Select Icelandair flight, departing Sat, Jul 4 from Fiumicino - Leonardo da Vinci Intl. to O'Hare Intl., returning Sat, Jul 18, priced at $728 found 3 days ago