Vacation Packages in Chicago
2 travelers
Boston (BOS)
Chicago, IL
Thu 8/8
Thu 8/15
When is the best time to fly to Chicago?
Determine the best time to fly to Chicago based on the average flight price by month. Price data was last updated on Thu Jul 25 2024
January
$248
February
$245
March
$280
April
$258
May
$278
June
$308
July
$304
August
$268
September
$255
October
$248
November
$268
December
$248
Tips for booking hotels in Chicago
Gain useful insights to help choose a hotel in Chicago. Data was last updated on Thu Jul 25 2024.
| Cheapest month: | January |
|---|---|
| Most expensive month: | October |
| Average price in Chicago: | $242/night |
| Cheapest price found: | $24/night |
| Cheapest day: | Sunday |
| Most expensive day: | Saturday |
$166 - $316
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.$240 - $286
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 Thu Jul 25 2024.
165 East Ontario Street, Chicago, IL, United States
0.0 mi from city centre
Pool
Free Wi-Fi
$1,667
Avg. per night
660 North State Street, Chicago, IL, United States
0.0 mi from city centre
Free Wi-Fi
$1,606
Avg. per night
$2,699
Avg. per night
1331 N Wicker Park Ave, Chicago, IL, United States
0.0 mi from city centre
Free Wi-Fi
$2,097
Avg. per night
300 East Ohio Street, Chicago, IL, United States
0.0 mi from city centre
Free Wi-Fi
$1,915
Avg. per night
7434 East State Street, Rockford, IL, United States
0.0 mi from city centre
Free Wi-Fi
Parking
$484
Avg. per night
$1,568
Avg. per night
933 West Belmont Avenue, Chicago, IL, United States
0.0 mi from city centre
Free Wi-Fi
$1,310
Avg. per night
111 West Huron Street, Chicago, IL, United States
0.0 mi from city centre
Free Wi-Fi
$1,307
Avg. per night
6401 West Touhy Avenue, Chicago, IL, United States
0.0 mi from city centre
Free Wi-Fi
Parking
Air Conditioning
$531
Avg. per night