Search Deals onDarien Vacation Packages
Darien Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Riverview Inn & Suites, an Ascend Collection Hotel
Save 100% on your flight
Price was $418, price is now $295 per person
$295
per person
Oct 29 - Nov 2
found 1 day ago
Roundtrip flight included
Houston (HOU) to Chicago (ORD)
Book a stay at this business-friendly hotel in Rockford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Boylan Tennis Center and Anderson Japanese Gardens are located nearby.
Staff were very friendly and helpful. Room had no issues.
Reviewed on Aug 25, 2026
Level Chicago – Old Town
Save 100% on your flight
Price was $1,087, price is now $641 per person
$641
per person
Nov 5 - Nov 9
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.
The Emily Hotel
Save 100% on your flight
Price was $1,624, price is now $1,028 per person
$1,028
per person
Oct 28 - Nov 3
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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $1,049, price is now $673 per person
$673
per person
Nov 5 - Nov 9
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, 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.
The Peninsula Chicago
Save 100% on your flight
Price was $2,835, price is now $1,911 per person
$1,911
per person
Oct 28 - Nov 3
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.
The service and the staff iare incredible, do professional!!
So many details!
My husband and I were so happy!!
Reviewed on Aug 25, 2026
Sentral Michigan Avenue
Save 100% on your flight
Price was $1,185, price is now $827 per person
$827
per person
Oct 28 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly aparthotel in Chicago. Enjoy a 24-hour fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.
Pool was closed both days I stayed
Reviewed on Aug 24, 2026
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,446, price is now $1,016 per person
$1,016
per person
Oct 22 - Oct 25
found 5 hours 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.
❤️
Reviewed on Aug 26, 2026
voco Chicago Downtown - Riverwalk by IHG
Save 100% on your flight
Price was $1,437, price is now $1,020 per person
$1,020
per person
Oct 27 - Nov 3
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 breakfast and the pool 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, Oct 15 - Tue, Oct 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$148 Roundtrip, found 2 hours ago
$148
Roundtrip
found 2 hours ago
Sat, Sep 26 - Wed, Sep 30
LAX
Los Angeles Intl.
MDW
Midway Intl.
$230 Roundtrip, found 3 hours ago
$230
Roundtrip
found 3 hours ago
Fri, Nov 13 - Mon, Nov 30
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,082 Roundtrip, found 4 days ago
$1,082
Roundtrip
found 4 days ago
Tue, Sep 1 - Fri, Sep 18
PEK
Capital Intl.
ORD
O'Hare Intl.
$1,206 Roundtrip, found 13 hours ago
$1,206
Roundtrip
found 13 hours ago
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