Search Deals onChicago Vacation Packages
Chicago Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Save 100% on your flight
per person
May 3 - May 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
Congress Plaza Hotel
Save 100% on your flight
per person
Apr 30 - May 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Art Institute of Chicago are located nearby.
The Chicago Hotel Collection - Wrigleyville
Save 100% on your flight
per person
May 15 - May 20
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Stay at this 3.5-star hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and room service. Our guests praise the clean rooms in our reviews. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
Fairmont Chicago at Millennium Park
Save 100% on your flight
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). 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
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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.
Dorothy's
Save 100% on your flight
per person
Apr 30 - May 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Stay at this 3-star B&B in Chicago. Enjoy free breakfast, free WiFi, and laundry facilities. Popular attractions Wrigley Field and Michigan Avenue are located nearby.
La Banque Hotel
Save 100% on your flight
per person
Jun 1 - Jun 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Stay at this 4-star golf hotel in Homewood. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby.
The Whitehall Hotel, BW Premier Collection
Save 100% on your flight
per person
Apr 30 - May 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Stay at this 3.5-star boutique hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the restaurant and 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.
Mon, May 12 - Wed, May 21
LGA
LaGuardia
ORD
O'Hare Intl.
$70 Roundtrip, found 2 days ago
$70
Roundtrip
found 2 days ago
Mon, May 12 - Tue, May 13
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$94 Roundtrip, found 6 days ago
$94
Roundtrip
found 6 days ago
Tue, Apr 15 - Tue, Apr 15
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$103 Roundtrip, found 19 hours ago
$103
Roundtrip
found 19 hours ago
Tue, Apr 8 - Sat, Apr 19
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$103 Roundtrip, found 20 hours ago
$103
Roundtrip
found 20 hours ago
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