Search Deals onChicago Vacation Packages
Chicago Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hampton Inn Chicago-Carol Stream
Save 100% on your flight
per person
Jun 20 - Jun 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this hotel in Carol Stream. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Cosley Zoo and Dupage County Historical Museum are located nearby.
The Allegro Royal Sonesta Hotel Chicago Loop
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Kimpton Gray Hotel by IHG
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4.5-star 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 Art Institute of Chicago and Chicago Riverwalk are located nearby.
Swissotel - Chicago
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
InterContinental Chicago Magnificent Mile by IHG
Save 100% on your flight
per person
Jul 4 - Jul 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
EVEN Hotel Chicago Tinley Park-Conv Ctr by IHG
Save 100% on your flight
per person
Jun 24 - Jun 29
found 3 hours ago
Roundtrip flight included
Las Vegas (LAS) to Chicago (ORD)
Stay at this 3.5-star business-friendly hotel in Tinley Park. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Odyssey Fun World and Credit Union 1 Amphitheatre are located nearby.
Congress Plaza Hotel
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
L7 Chicago by LOTTE
Save 100% on your flight
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Book a stay at this boutique 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 Chicago Riverwalk and Michigan Avenue 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.
Fri, May 30 - Mon, Jun 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$62 Roundtrip, found 7 hours ago
$62
Roundtrip
found 7 hours ago
Sat, Jun 7 - Mon, Jun 9
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$80 Roundtrip, found 17 hours ago
$80
Roundtrip
found 17 hours ago
Sun, May 25 - Thu, May 29
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$88 Roundtrip, found 7 hours ago
$88
Roundtrip
found 7 hours ago
Tue, May 27 - Tue, Jun 3
LGA
LaGuardia
ORD
O'Hare Intl.
$90 Roundtrip, found 4 days ago
$90
Roundtrip
found 4 days ago
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