Vacation Packages in Chicago
From
Boston (BOS)
To
Chicago, United States
2 adults, no children
We work with more than 300 partners to bring you better travel deals
Tips for booking hotels in Chicago
Gain useful insights to help choose a hotel in Chicago. Data was last updated on Wed Apr 30 2025.
| Cheapest month: | January |
|---|---|
| Most expensive month: | October |
| Average price in Chicago: | $259/night |
| Cheapest price found: | $26/night |
| Cheapest day: | Sunday |
| Most expensive day: | Friday |
$167 - $394
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.$223 - $251
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.Popular Chicago vacation deals
Users browsing Cheapflights choose these vacation package deals more than any other. Data was last updated on Wed Apr 30 2025.
9625 South 76th Avenue, Bridgeview, IL, United States
0.0 mi from city centre
Free Wi-Fi
Parking
$527
Avg. per night
1550 McConnor Parkway, Schaumburg, IL, United States
0.0 mi from city centre
Pool
Free Wi-Fi
Parking
$911
Avg. per night
10 East Grand Avenue, Chicago, IL, United States
0.0 mi from city centre
Pool
Free Wi-Fi
$1,047
Avg. per night
6650 South Cicero Avenue, Bedford Park, IL, United States
0.0 mi from city centre
Free Wi-Fi
Air Conditioning
$687
Avg. per night
1150 North Arlington Heights Road, Itasca, IL, United States
0.0 mi from city centre
Pool
Free Wi-Fi
Parking
$819
Avg. per night
2881 Touhy Avenue, Elk Grove Village, IL, United States
0.0 mi from city centre
Free Wi-Fi
Parking
Air Conditioning
$490
Avg. per night
1801 Milwaukee Avenue, Glenview, IL, United States
0.0 mi from city centre
Pool
Free Wi-Fi
Parking
$949
Avg. per night
108 East Superior Street, Chicago, IL, United States
0.0 mi from city centre
Pool
Free Wi-Fi
$4,294
Avg. per night
5500 North River Road, Rosemont, IL, United States
0.0 mi from city centre
Pool
$1,193
Avg. per night
6630 South Cicero Avenue, Bedford Park, IL, United States
0.0 mi from city centre
Pool
Free Wi-Fi
$966
Avg. per night