Search Deals onChicago Vacation Packages
Chicago Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
per person
May 9 - May 11
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Spark by Hilton Stevensville
Save 100% on your flight
per person
May 22 - May 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Book a stay at this business-friendly hotel in Stevensville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Silver Beach and Grand Mere State Park are located nearby.
Thompson Chicago, by Hyatt
Save 100% on your flight
per person
May 14 - May 18
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 bars/lounges, and room service. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Glen Club
Save 100% on your flight
per person
Jun 12 - Jun 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
Stay at this 3.5-star golf hotel in Glenview. Enjoy free WiFi, free parking, and a golf course. Our guests praise the helpful staff in our reviews. Popular attractions The Glen Club and Kohl Children's Museum are located nearby.
The Boulevard Inn & Bistro
Save 100% on your flight
per person
May 22 - May 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Stay at this 3.5-star hotel in Saint Joseph. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Silver Beach and FuzzyButz Pet Bakery are located nearby.
The Chicago Hotel Collection - Magnificent Mile
Save 100% on your flight
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
Stay at this 4-star boutique hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, 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.
Hampton Inn Chicago/Naperville
Save 100% on your flight
per person
Jun 19 - Jun 26
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Book a stay at this business-friendly hotel in Naperville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Naperville Yard Indoor Sports Complex and Nike Sports Complex are located nearby.
L7 Chicago by LOTTE
Save 100% on your flight
per person
May 14 - May 18
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.
Tue, Jun 17 - Wed, Jun 18
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$78 Roundtrip, found 5 hours ago
$78
Roundtrip
found 5 hours ago
Sat, Apr 26 - Wed, Apr 30
LGA
LaGuardia
ORD
O'Hare Intl.
$81 Roundtrip, found 5 days ago
$81
Roundtrip
found 5 days ago
Sun, May 4 - Thu, May 8
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$83 Roundtrip, found 3 days ago
$83
Roundtrip
found 3 days ago
Wed, May 14 - Tue, May 20
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$84 Roundtrip, found 17 hours ago
$84
Roundtrip
found 17 hours ago
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