Search Deals onNorthwest Chicago Vacation Packages
Northwest Chicago Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Save 100% on your flight
Price was $1,090, price is now $753 per person
$753
per person
Jul 8 - Jul 11
found 1 day ago
Roundtrip flight included
Dallas (DAL) 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.
LondonHouse Chicago, Curio Collection by Hilton
Save 100% on your flight
Price was $2,600, price is now $1,646 per person
$1,646
per person
Jul 29 - Aug 3
found 2 hours ago
Roundtrip flight included
Dallas (DAL) 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.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $1,150, price is now $774 per person
$774
per person
Jun 28 - Jul 2
found 1 hour ago
Roundtrip flight included
Mesa (AZA) 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.
Trump International Hotel & Tower Chicago
Save 100% on your flight
Price was $2,603, price is now $1,763 per person
$1,763
per person
Jul 29 - Aug 3
found 2 hours ago
Roundtrip flight included
Dallas (DAL) 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.
Viceroy Chicago
Save 100% on your flight
Price was $2,227, price is now $1,520 per person
$1,520
per person
Jul 29 - Aug 3
found 2 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Kimpton Gray Hotel by IHG
Save 100% on your flight
Price was $2,167, price is now $1,483 per person
$1,483
per person
Jul 29 - Aug 3
found 2 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Lodge Geneva National
Save 100% on your flight
Price was $1,598, price is now $1,102 per person
$1,102
per person
Jun 23 - Jun 29
found 10 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Chicago (ORD)
Book a stay at this golf resort in Lake Geneva. Enjoy an outdoor pool, breakfast (surcharge), and a fitness center. Our guests praise the pool and the restaurant in our reviews. Popular attractions Geneva Lake and Geneva National Golf Club are located nearby.
Wind Creek Southland Casino and Hotel
Save 100% on your flight
Price was $1,096, price is now $773 per person
$773
per person
Jul 2 - Jul 6
found 12 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
Book a stay at this spa resort in Hazel Crest. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Midwest Carvers Museum and Ravisloe Country Club are located nearby.
Northwest Chicago Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Northwest Chicago 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, Jul 4 - Wed, Jul 8
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$158 Roundtrip, found 8 hours ago
$158
Roundtrip
found 8 hours ago
Wed, Jul 22 - Wed, Jul 29
LAX
Los Angeles Intl.
MDW
Midway Intl.
$239 Roundtrip, found 2 days ago
$239
Roundtrip
found 2 days ago
Wed, Jul 8 - Thu, Jul 16
FCO
Fiumicino - Leonardo da Vinci Intl.
ORD
O'Hare Intl.
$874 Roundtrip, found 11 hours ago
$874
Roundtrip
found 11 hours ago
Tue, Jun 2 - Mon, Sep 7
PVG
Pudong Intl.
ORD
O'Hare Intl.
$1,173 Roundtrip, found 11 hours ago
$1,173
Roundtrip
found 11 hours ago
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