Search Deals onChicago Vacation Packages
Chicago Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Save 100% on your flight
Price was $334, price is now $206 per person
$206
per person
Feb 27 - Mar 2
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Emily Hotel
Save 100% on your flight
Price was $622, price is now $361 per person
$361
per person
Feb 27 - Mar 2
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, 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.
Hotel Riu Plaza Chicago
Save 100% on your flight
Price was $657, price is now $386 per person
$386
per person
Mar 4 - Mar 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 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 $990, price is now $589 per person
$589
per person
Mar 18 - Mar 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.
Level Chicago – Old Town
Save 100% on your flight
Price was $506, price is now $304 per person
$304
per person
Feb 27 - Mar 2
found 2 days 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.
Pendry Chicago
Save 100% on your flight
Price was $481, price is now $293 per person
$293
per person
Feb 27 - Mar 2
found 2 days 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.
Hilton Chicago
Save 100% on your flight
Price was $530, price is now $330 per person
$330
per person
Feb 27 - Mar 2
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Soldier Field are located nearby.
Hilton Grand Vacations Club Chicago Magnificent Mile
Save 100% on your flight
Price was $471, price is now $293 per person
$293
per person
Feb 27 - Mar 2
found 2 days 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.
Chicago Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
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.
Wed, Jan 14 - Thu, Jan 22
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$68 Roundtrip, found 3 days ago
$68
Roundtrip
found 3 days ago
Wed, Jan 14 - Sat, Jan 17
LGA
LaGuardia
ORD
O'Hare Intl.
$72 Roundtrip, found 22 hours ago
$72
Roundtrip
found 22 hours ago
Mon, Feb 9 - Sat, Feb 21
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$79 Roundtrip, found 3 days ago
$79
Roundtrip
found 3 days ago
Sat, Jan 17 - Thu, Jan 22
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$82 Roundtrip, found 14 hours ago
$82
Roundtrip
found 14 hours ago
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