Search Deals onChicago Vacation Packages
Chicago Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Save 100% on your flight
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Stay at this 4-star 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.
The Royal Sonesta Chicago River North
Save 100% on your flight
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Stay at this 4.5-star 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.
Trump International Hotel & Tower Chicago
Save 100% on your flight
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Stay at this 5-star 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.
Palmer House a Hilton Hotel
Save 100% on your flight
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
The Allegro Royal Sonesta Hotel Chicago Loop
Save 100% on your flight
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Level Chicago – Old Town
Save 100% on your flight
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Stay at this 4-star spa aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Swissotel - Chicago
Save 100% on your flight
per person
Jul 27 - Jul 30
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Book a stay at this eco-certified hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park 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.
Tue, Jul 8 - Wed, Jul 9
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$63 Roundtrip, just found
$63
Roundtrip
just found
Tue, Sep 9 - Tue, Sep 9
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$92 Roundtrip, found 1 day ago
$92
Roundtrip
found 1 day ago
Wed, Jul 9 - Tue, Jul 15
LGA
LaGuardia
ORD
O'Hare Intl.
$92 Roundtrip, found 21 hours ago
$92
Roundtrip
found 21 hours ago
Tue, Jul 22 - Wed, Jul 30
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$108 Roundtrip, just found
$108
Roundtrip
just found
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