A Travel Price Comparison for United States of America Chicago vs. Woodstock for Vacations, Tours, and Honeymoons

Should you visit Chicago or Woodstock?

Which is cheaper to visit? Which is more expensive for vacation?

Which city is more affordable and which is best for your travel style? If you're trying to figure out where to go next, comparing the travel costs between Chicago and Woodstock can help you decide which place is right for you.

Where Should I go: Chicago or Woodstock?

Chicago

Located in the Midwest, Chicago is the third largest city in the United States. It has a population of almost 3 million and a metropolitan area that covers more than 10,000 square kilometers. It is also a hub for music, comedy and theater. It's skyline is beautiful with modern skyscrapers and Lake Michigan as a backdrop. It is easy to stay entertained in Chicago for weeks. There are world class museums, upscale or eclectic shopping opportunities, and impressive architecture.

Woodstock

While this town does lend its name to the 1969 Woodstock Festival, the legendary event was actually held on a dairy farm almost 60 miles away in Bethel, NY. So if you are looking to see the field where it all happened and a museum dedicated to its history, you will need to take a day trip outside of town.

Woodstock, New York, however, does stay true to the spirit of the arts. Since 1903, the place lay home to Byrdcliffe Art Colony, the oldest of its kind in the nation, and even attracted artists of the Hudson River School during the late 1800s. Today, artists from all disciplines-visual, ceramic, music, fiction, nonfiction, screenwriting, playwriting, and poetry-take up residence at the colony and have works displayed in galleries open in the main part of town.

Tinker Street and Mill Hill Road are lined with a mix of restaurants and shops all teeming with the essence of hippie living, arts, and spirituality. From shops selling Woodstock paraphernalia, incense, and Himalayan products, to yoga studios, vegan restaurants, and local art galleries-the town of Woodstock is one dedicated to keeping the spirit of the Woodstock Festival and the arts alive.

For some great organized tour ideas, see The Best Family-Friendly Tours to United States of America, The Best Wildlife Tours to United States of America, The Best Hiking & Trekking Tours in United States of America, and The Best Historical Tours in United States of America.


Which place is cheaper, Woodstock or Chicago?

These are the overall average travel costs for the two destinations.

The average daily cost (per person) in Chicago is $288, while the average daily cost in Woodstock is $154. These costs include accommodation (assuming double occupancy, so the traveler is sharing the room), food, transportation, and entertainment. While every person is different, these costs are an average of past travelers in each destination. What follows is a categorical breakdown of travel costs for Chicago and Woodstock in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Chicago $198
    Woodstock $81
  • Accommodation Typical double-occupancy room
    Chicago $396
    Woodstock $162
Compare Hotels in Chicago and Woodstock

Looking for a hotel in Chicago or Woodstock? Prices vary by location, date, season, and the level of luxury. See below for options and compare which is best for your budget and travel style.

Hotels in Chicago


Hotels in Woodstock


Kayak helps you find the best prices for hotels, flights, and rental cars for destinations around the world. Compare prices for multiple destinations when planning your next trip.


Our Analysis
We've analyzed the average and typical hotel prices based on guest reviews, star ratings, and hotel amenities here: Chicago Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Chicago $37
    Woodstock $60
Typical Local Transportation Prices in Chicago

Here are some examples of typical transportation prices from actual travelers in Chicago:


  • Parking
    $19
  • Taxi Ride
    $10
  • Taxi from Airport
    $45

Hired Cars and Shuttles in Chicago

Some specific examples of transportation prices in Chicago:

  • Chicago O´Hare International Airport Private Transfer One-Way: $27
  • Airport transfer between Chicago O'Hare and Milwaukee: $38
  • Private Arrival Transfer from Chicago Airports ORD Or MDW: $50
  • Chicago Midway Airport (MDW) to Chicago hotel/address - Arrival Private Transfer: $53
  • Chicago to Chicago O'Hare Airport (ORD) - Departure Private Car Transfer: $64
  • ORD Airport Private Transfer to/from Chicago: $81
  • Private One-Way ORD Airport Transfer: $87
  • Private Transfer Chicago to Chicago Airport by Luxury Car or SUV: $87
  • Private Arrival Transfer from Chicago Airports (ORD) (MDW): $90
  • Private Departure Transfer to Chicago Airports (ORD)(MDW): $90
  • MDW Airport Private Transfer to/from Chicago: $100
  • Chicago Midway Airport (MDW) to Chicago City - Round-Trip Private Transfer: $106

Is it cheaper to fly into Chicago or Woodstock?

Prices for flights to both Woodstock and Chicago change regularly based on dates and travel demand. We suggest you find the best prices for your next trip on Kayak, because you can compare the cost of flights across multiple airlines for your prefered dates.





Food
  • Food Meals for one day
    Chicago $49
    Woodstock $34
Typical Food Prices in Chicago

Below are a few samples from actual travelers for food and meal costs in Chicago:


  • Dinner for 1
    $24
  • Dinner for 3
    $118

Food Tours and Cooking Classes in Chicago

Also, here are some specific examples of food and dining related activities in Chicago.

  • Traveling Spoon Chicago-Style Deep Dish Pizza Private Online Cooking Class : $40
  • Chicago : Hands-on Cooking Classes With Local Chef: $55
  • Chicago Small Group Food Tour: $69
  • Lake Michigan Gourmet Brunch/Lunch/Dinner Cruise: $72
  • Downtown Pizza Guided Walking Tour with Tastings: $73
  • Chicago Deep Dish Pizza Self-Guided Tour: $75
  • Chicago West Loop Pizza Crawl: $79
  • Chicago Bucktown-Wicker Park Pizza Crawl: $79
  • Downtown Family Food Tour by Bike with Sightseeing: $80
  • Nitti's Supper Club Dinner and Show: $80
  • Lake Michigan Buffet Brunch, Lunch or Dinner Cruise: $86
  • Secret Food Tour: $88

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Chicago $47
    Woodstock $35
Typical Entertainment Prices in Chicago

Here are a few typical costs in Chicago for activities, ticket prices, and tours that come from previous visitors:


  • Sears Tower (family of 4)
    $102
  • Aquarium for 4
    $118
  • Water Taxi (family of 4)
    $22
  • IMAX Movie for Two
    $35
  • Shakespeare Play (2)
    $116
  • Art Institute (2)
    $36
  • U-Boat Tour (2)
    $8.00

Tours and Activities in Chicago

Here are a few actual costs in Chicago for available activities, ticket prices, and tours:

  • Discovering Chicago with Walking In App Audio Tour: $6.00
  • Haunted Sites Self-Guided Audio Walking Tour: $6.50
  • Chicago’s Ragtime & Jazz Eras: A Self-Guided Audio Tour: $6.99
  • Vice, Crime and Gangsters Self-Guided Audio Tour: $6.99
  • Vice, Crime and Gangsters in A Self-Guided Audio Tour: $6.99
  • Must-Sees & Hidden Gems In-App Audio Tour (ENG): $9.00
  • App Chicago self-guided tours with multilingual audioguides: $9.76
  • Scavenger Hunt Adventure Self-Guided City Game: $10
  • Uncover Mysteries: Gold Coast Self-Guided Audio Tour: $11
  • Self-Guided Audio Tour: $11
  • Discover La Jolla's Charms: A Self-Guided Audio Tour: $11
  • The Loop, River North and Chicago’s Theater District: A Self-Guided Audio Tour: $12

For more ideas for your next trip, check out The Best Free Things to Do in Chicago, Chicago Bucket List: The Best Places to See, and The Best Museums in Chicago.


Alcohol
  • Alcohol Drinks for one day
    Chicago $25
    Woodstock $22

Sample the Local Flavors in Chicago

Here are a few nightlife and alcohol tours and activities from local tour providers in Chicago:

  • Chicago Walking Brewery Tour in Malt Row: $15
  • Malt Row Walking Brewery Tour: $30
  • Walking tour to Chicago dive bars: $41
  • Chicago Craft Brewery Barrel Bus Tour: $100
  • Craft Brewery Tour by Barrel Bus: $100


When we compare the travel costs of actual travelers between Chicago and Woodstock, we can see that Chicago is more expensive. And not only is Woodstock much less expensive, but it is actually a significantly cheaper destination. So, traveling to Woodstock would let you spend less money overall. Or, you could decide to spend more money in Woodstock and be able to afford a more luxurious travel style by staying in nicer hotels, eating at more expensive restaurants, taking tours, and experiencing more activities. The same level of travel in Chicago would naturally cost you much more money, so you would probably want to keep your budget a little tighter in Chicago than you might in Woodstock.

If you're trying to decide if either of these two destinations are within your price range, also see Is Chicago Expensive? and Is Woodstock Expensive?.


Which is Bigger, Chicago or Woodstock?

Chicago has a larger population, and is about 1300 times larger than the population of Woodstock. When comparing the sizes of Chicago and Woodstock, keep in mind that a larger population does not always imply the destination has more attractions or better activities. So, always research the type of place that you want to visit along with the activities and attractions that interest you.


When is the best time to visit Chicago or Woodstock?

Both destinations experience a temperate climate with four distinct seasons. And since both cities are in the northern hemisphere, summer is in July and winter is in January.

Should I visit Chicago or Woodstock in the Summer?

The summer attracts plenty of travelers to both Chicago and Woodstock. Most visitors come to Chicago for the beaches, the city activities, the music scene, and the family-friendly experiences during these months.

In the summer, Chicago is around the same temperature as Woodstock. Typically, the summer temperatures in Chicago in July average around 77°F (25°C), and Woodstock averages at about 74°F (24°C).

People are often attracted to the plentiful sunshine in Woodstock this time of the year. In Chicago, it's very sunny this time of the year. Chicago usually receives more sunshine than Woodstock during summer. Chicago gets 326 hours of sunny skies, while Woodstock receives 293 hours of full sun in the summer.

Chicago gets a good bit of rain this time of year. In July, Chicago usually receives more rain than Woodstock. Chicago gets 3.9 inches (100 mm) of rain, while Woodstock receives 3.4 inches (87 mm) of rain each month for the summer.


  • Summer Average Temperatures July
    Chicago 77°F (25°C) 
    Woodstock 74°F (24°C)

Should I visit Chicago or Woodstock in the Autumn?

The autumn brings many poeple to Chicago as well as Woodstock. The autumn months attract visitors to Chicago because of the city's sights and attractions, the shopping scene, the music scene, and the natural beauty of the area.

In October, Chicago is generally a little warmer than Woodstock. Daily temperatures in Chicago average around 56°F (14°C), and Woodstock fluctuates around 53°F (12°C).

In the autumn, Chicago often gets around the same amount of sunshine as Woodstock. Chicago gets 195 hours of sunny skies this time of year, while Woodstock receives 197 hours of full sun.

Chicago usually gets less rain in October than Woodstock. Chicago gets 2.2 inches (56 mm) of rain, while Woodstock receives 3 inches (77 mm) of rain this time of the year.


  • Autumn Average Temperatures October
    Chicago 56°F (14°C) 
    Woodstock 53°F (12°C)

Should I visit Chicago or Woodstock in the Winter?

Both Woodstock and Chicago are popular destinations to visit in the winter with plenty of activities. The museums, the Christmas ambience, the shopping scene, the theater shows, and the cuisine are the main draw to Chicago this time of year.

Be prepared for some very cold days in Woodstock. It's quite cold in Chicago in the winter. Chicago is around the same temperature as Woodstock in the winter. The daily temperature in Chicago averages around 25°F (-4°C) in January, and Woodstock fluctuates around 25°F (-4°C).

Chicago usually receives less sunshine than Woodstock during winter. Chicago gets 134 hours of sunny skies, while Woodstock receives 167 hours of full sun in the winter.

In January, Chicago usually receives less rain than Woodstock. Chicago gets 1.9 inches (47 mm) of rain, while Woodstock receives 3.3 inches (83 mm) of rain each month for the winter.


  • Winter Average Temperatures January
    Chicago 25°F (-4°C) 
    Woodstock 25°F (-4°C)

Should I visit Chicago or Woodstock in the Spring?

Both Woodstock and Chicago during the spring are popular places to visit. Many travelers come to Chicago for the beaches, the activities around the city, and the natural beauty.

In the spring, Chicago is a little warmer than Woodstock. Typically, the spring temperatures in Chicago in April average around 52°F (11°C), and Woodstock averages at about 49°F (10°C).

In Woodstock, it's very sunny this time of the year. It's quite sunny in Chicago. In the spring, Chicago often gets around the same amount of sunshine as Woodstock. Chicago gets 218 hours of sunny skies this time of year, while Woodstock receives 227 hours of full sun.

It rains a lot this time of the year in Chicago. Chicago usually gets more rain in April than Woodstock. Chicago gets 4.3 inches (108 mm) of rain, while Woodstock receives 3.7 inches (95 mm) of rain this time of the year.


  • Spring Average Temperatures April
    Chicago 52°F (11°C) 
    Woodstock 49°F (10°C)

Typical Weather for Woodstock and Chicago

Chicago Woodstock
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 25°F (-4°C) 1.9 inches (47 mm) 25°F (-4°C) 3.3 inches (83 mm)
Feb 29°F (-2°C) 1.4 inches (35 mm) 28°F (-2°C) 3.2 inches (81 mm)
Mar 41°F (5°C) 3.7 inches (93 mm) 38°F (3°C) 3.8 inches (97 mm)
Apr 52°F (11°C) 4.3 inches (108 mm) 49°F (10°C) 3.7 inches (95 mm)
May 63°F (17°C) 3 inches (75 mm) 60°F (16°C) 3.5 inches (89 mm)
Jun 73°F (23°C) 3.9 inches (100 mm) 69°F (21°C) 3.5 inches (90 mm)
Jul 77°F (25°C) 3.9 inches (100 mm) 74°F (24°C) 3.4 inches (87 mm)
Aug 76°F (24°C) 3.5 inches (90 mm) 72°F (22°C) 3.9 inches (100 mm)
Sep 68°F (20°C) 3.8 inches (96 mm) 64°F (18°C) 3.5 inches (90 mm)
Oct 56°F (14°C) 2.2 inches (56 mm) 53°F (12°C) 3 inches (77 mm)
Nov 44°F (7°C) 2.2 inches (56 mm) 43°F (6°C) 4.3 inches (110 mm)
Dec 31°F (-1°C) 2.8 inches (71 mm) 30°F (-1°C) 4.1 inches (103 mm)