The average price of a 7-day trip to Westchester is $1,451 for a solo traveler, $2,606 for a couple, and $4,886 for a family of 4. Westchester hotels range from $54 to $246 per night with an average of $75, while most vacation rentals will cost $140 to $440 per night for the entire home. Average worldwide flight costs to Chicago Midway International Airport (MDW) are between $665 and $1,066 per person for economy flights and $2,087 to $3,345 for first class. Depending on activities, we recommend budgeting $40 to $84 per person per day for transportation and enjoying local restaurants.
See below for average, budget, and luxury trip costs. You can also look up flight costs from your airport for more tailored flight pricing.
The Cheapest Times to Visit Westchester, IL, US
On average, these will be the cheapest dates to fly to MDW and stay in a Westchester hotel:
- January 8th to March 11th
- August 6th to December 9th (except the week of November 26th)
The absolute cheapest time to take a vacation in Westchester is usually mid to late September.
Average Westchester Trip Costs
Average Solo Traveler
The average cost for one person to visit Westchester for a week is $1,173-$2,199($168-$314 per day)
Food, Travel, and Sightseeing: $40 to $84 per day for one person’s daily expenses
Flights: $443 to $927 for economy
Lodging: $75 to $104 per night for one 2 or 3-star hotel room
or $94 to $114 per night for a 1-bed vacation rental
Average Couple’s Trip
The average cost for a couple to visit Westchester for a week is $2,340-$3,992($334-$570 per day)
Food, Travel, and Sightseeing: $80 to $168 per day for two people’s daily expenses
Flights: $886 to $1,854 for economy
Lodging: $75 to $104 per night for one 2 or 3-star hotel room
or $94 to $114 per night for a 1-bed vacation rental
Average Family Vacation
The average cost for 4 people to visit Westchester for a week is $3,684-$7,308($526-$1,044 per day)
Food, Travel, and Sightseeing: $160 to $336 per day for four people’s daily expenses
Flights: $1,772 to $3,708 for economy
Lodging: $150 to $208 per night for two 2 or 3-star hotel rooms
or $132 to $171 per night for a 2-bed vacation rental
Traveling Cheap to Westchester
How cheap can you make a vacation to Westchester? The cheapest trip to Westchester is about $100 per person per day for travelers willing to take standby flights, deal with inconvenience, and otherwise limit travel expenses. About 2% of rentals are available in the $0 to $100 range for an entire place, and vacation rentals can be booked for as low as $20 per night. These inexpensive rentals must be booked as early as possible and may not be in the most desirable areas. 1-star hotels are more likely to be available, with rooms starting at around $43.
Even cheaper trips are possible depending on where you live and whether you can drive. Check the cheapest times to fly for more saving ideas.
Budget Solo Traveler
The lowest cost for one person to visit Westchester for a week is $703-$1,538($100-$220 per day)
Food, Travel, and Sightseeing: $20 to $41 per day for one person’s daily expenses
Flights: $443 to $927 for economy
Lodging: $43 to $54 per night for one 1-star hotel room
or $20 to $50 per night for a 1-bed vacation rental
Budget Couple’s Trip
The lowest cost for a couple to visit Westchester for a week is $1,286-$2,752($184-$393 per day)
Food, Travel, and Sightseeing: $40 to $82 per day for two people’s daily expenses
Flights: $886 to $1,854 for economy
Lodging: $43 to $54 per night for one 1-star hotel room
or $20 to $50 per night for a 1-bed vacation rental
Budget Family Vacation
The lowest cost for 4 people to visit Westchester for a week is $2,500-$5,504($357-$786 per day)
Food, Travel, and Sightseeing: $80 to $164 per day for four people’s daily expenses
Flights: $1,772 to $3,708 for economy
Lodging: $86 to $108 per night for two 1-star hotel rooms
or $28 to $75 per night for a 2-bed vacation rental
Overall it is possible but not easy to travel to Westchester cheaply.
The Cost of a Luxury Westchester Trip
There is no true ceiling on the cost of a luxury trip, so our estimates are based on what most people do in Westchester.
Luxury Solo Traveler
The high-end price for one person to visit Westchester for a week is $2,519-$8,557($360-$1,222 per day)
Food, Travel, and Sightseeing: $72 to $151 per day for one person’s daily expenses
Flights: $1,325 to $1,956 for first class
Lodging: $115 to $246 per night for one 4 or 5-star hotel room
or $440 to $924 per night for a preferred vacation rental
Luxury Couple’s Trip
The high-end price for a couple to visit Westchester for a week is $4,348-$11,570($621-$1,653 per day)
Food, Travel, and Sightseeing: $144 to $302 per day for two people’s daily expenses
Flights: $2,650 to $3,912 for first class
Lodging: $115 to $246 per night for one 4 or 5-star hotel room
or $440 to $924 per night for a preferred vacation rental
Luxury Family Vacation
The high-end price for 4 people to visit Westchester for a week is $8,696-$20,368($1,242-$2,910 per day)
Food, Travel, and Sightseeing: $288 to $604 per day for four people’s daily expenses
Flights: $5,300 to $7,824 for first class
Lodging: $230 to $492 per night for two 4 or 5-star hotel rooms
or $660 to $1,386 per night for a preferred vacation rental
Westchester Hotel Prices
The cost of staying in Westchester is about average than the average city. On average hotels are less expensive than vacation rentals. Luxury vacation rentals are more expensive in Westchester due to very high property costs. The graphs below show how much cost can vary depending on the type of experience you’re looking for.
Westchester Lodging Cost by Star Status
The average price for the class of hotel is on the (y) axis. The hotel class (out of 5 stars) is on the (x) axis.
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Prices are based on Westchester hotel averages and may not reflect current prices. In some cases, we extrapolate prices to estimate costs, and hotels with your desired star rating may not be available.
Vacation Rental Prices
The percent of vacation rentals in the price range is on the left (y) axis. Price range is on the bottom (x) axis.
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There are a healthy amount of vacation rentals serving all budgets in Westchester.
Flight Costs to Westchester
Averaging flights around the world, prices go from a high of $1,066 average in late July to a low of $665 in mid to late September. Median flight price is $629. These prices are based on millions of flights. For Westchester our data includes 642 originating airports, and 109 airlines. The area has more variance in price compared with other locations. Flying to Westchester from an airport like Saarbruecken (SCN) in Saarbrucken (Germany) for an average $6,688 trip fare will obviously cost a lot more than from an airport like Manistee County-Blacker (MBL) in Manistee/Ludington, MI (the United States) at an average of just $221.
Average Flight Cost by Season
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Average Flight Cost by Day of Week
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The cheapest day to fly in is typically Tuesday, and the cheapest day to fly back is usually Tuesday. Click here to see data for the cost of flights from your airport. In Westchester, the difference between the cheapest and the most expensive week is about $401, so you can easily save about 60% simply by using our free flight guides and booking in advance.
Daily Expenses Budget
Daily vacation expenses vary more based on what you’re interested in doing. A fine dining restaurant with drinks around Westchester can easily cost $310 per person or more, while a standard nice meal might be about $20 per person. Private tours can cost $612 per day, but self-guided tours to see the outdoor sights can be free. Costs vary wildly, so recommendations are made based on the cost of living and averages we see for this type of vacation.