Search Deals onDarien Vacation Packages
Darien Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Price was $354, price is now $245 per person
$245
per person
Dec 17 - Dec 20
found 2 days 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.
Nice updated property in a great location
Reviewed on Oct 9, 2026
Level Chicago – Old Town
Save 100% on your flight
Price was $1,005, price is now $619 per person
$619
per person
Dec 18 - Dec 22
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.
Great location, very clean, loved the gym and cafe!
Reviewed on Oct 10, 2026
Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination
Save 100% on your flight
Price was $1,150, price is now $717 per person
$717
per person
Dec 11 - Dec 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this business-friendly hotel in Joliet. Enjoy free WiFi, 3 restaurants, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Route 66 Raceway and Harrah's Casino are located nearby.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $508, price is now $326 per person
$326
per person
Dec 17 - Dec 20
found 2 days 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.
Great food, very helpful staff
Reviewed on Oct 10, 2026
Pendry Chicago
Save 100% on your flight
Price was $837, price is now $549 per person
$549
per person
Dec 3 - Dec 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.
Fantastic stay!
Reviewed on Oct 6, 2026
Hilton Grand Vacations Club Chicago Magnificent Mile
Save 100% on your flight
Price was $653, price is now $436 per person
$436
per person
Dec 29 - Jan 1
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 breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $693, price is now $463 per person
$463
per person
Dec 17 - Dec 20
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $1,158, price is now $804 per person
$804
per person
Dec 18 - Dec 21
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.
Darien Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Darien 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.
Thu, Dec 10 - Mon, Dec 14
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$193 Roundtrip, found 11 hours ago
$193
Roundtrip
found 11 hours ago
Thu, Nov 12 - Fri, Nov 13
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 2 hours ago
$197
Roundtrip
found 2 hours ago
Mon, Nov 9 - Fri, Nov 13
LAX
Los Angeles Intl.
MDW
Midway Intl.
$197 Roundtrip, found 3 hours ago
$197
Roundtrip
found 3 hours ago
Fri, Nov 13 - Wed, Dec 2
PVG
Pudong Intl.
ORD
O'Hare Intl.
$998 Roundtrip, found 10 hours ago
$998
Roundtrip
found 10 hours ago
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