A Travel Price Comparison for United States of America Orlando vs. Chicago for Food, Nightlife, Families, and Couples

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Should you visit Orlando or Chicago?

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

Should I visit Orlando or Chicago? This is a common question asked by many travelers. By figuring out which city has activities that align with your interests along with knowing which is more affordable, you'll understand where you can get more bang for your buck. So, let's dive into the details and the data, which all comes from actual travelers.

Orlando

Orlando is a active, family-friendly, and entertaining city. Other popular activities here include shopping, theater, and nightlife.

Chicago

Chicago is a cosmopolitan, diverse, and vibrant city. It's an amazing and huge city with tons of activities and things to do. It's a gorgeous place to visit. Other reasons to visit include museums, theater, and nightlife.

Orlando and Chicago: Pros and Cons

Orlando
Pros
  • Family-friendly
  • Good for couples and romance
Cons
  • Less theater options
  • Less popular for nightlife
  • Public transit not as usable
  • Less walkable
Chicago
Pros
  • Numerous theater shows
  • Good nightlife
  • Family-friendly
  • Good for couples and romance
  • Good public transit
  • Very walkable
  • Big city activities


How is Orlando different from Chicago?

Which is Better for a Holiday?

Let's take a look at the differences and similarities between Chicago and Orlando. Then, you can decide for yourself which place is better for your next trip.

Is Orlando or Chicago Better for Theater?

Orlando
Chicago

With more venues to choose from, Chicago is more regarded as a theater destination.

The theater and performance venues in Chicago draw crowds from around the world. Theater is big here with many of the major Broadway productions visiting the city. There is also an endless list of smaller, local theaters to choose from.

Orlando offers a number of shows and performances. The city has a number of local theaters that are fun to explore. As home to Disney World and Universal Studios, there are also a number of shows available that are affiliated with the parks.


Is Orlando or Chicago Better for Food?

Orlando
Chicago

There are opportunities to sample the local cuisine at great restaurants in both Orlando and Chicago.

The food selection at local restaurants is excellent in Orlando. There are a diversity of restaurants on the Disney grounds and nearby. Restaurants can be challenging though, as reservations must be made months in advance.

Chicago has long been recognized as a culinary destination with great restaurants. While you're in town you have to try the famous deep dish pizza, Chicago style hot dogs, and Italian beef.

Is Orlando or Chicago Better for Nightlife?

Orlando
Chicago

The nightlife vibe is much better in Chicago than Orlando.

Chicago is a destination that you simply have to visit at least once for nightlife. Popular bars and clubs include the Smart Bar, Beauty Bar, and Le Nocturne.

There's a variety of activities in the evening in Orlando. If you need a break from the kids, you'll find some of the best nightlife around Orlando at Disney Springs, Wall Street Plaza and Universal CityWalk.

Is Orlando or Chicago Better for Shopping?

Orlando
Chicago

If you're looking to go shopping, Orlando and Chicago both offer plenty of spots.

Shopping is a popular activity when visiting Orlando. Shopping is a dream for any Disney enthusiast. There are countless malls and shops, both on and off the Disney grounds, that sell all of the Disney paraphernalia.

The abundance of shops in Chicago make it a world-class shopping destination. The most famous shopping area is Michigan Avenue and the famous Magnificent Mile.

Is Orlando or Chicago Better for Christmas?

Orlando
Chicago

With various activities, both Orlando and Chicago are good places to visit during Christmas.

With so many activities, Orlando is a top place to visit during Christmas. Christmas at Disney World is lots of fun. There are decorations and all kinds of seasonal activities around town.

Chicago is an extremely popular place to visit during the Christmas season. There's a number of seasonal celebrations, ice skating, and excellent shopping.


Is Orlando or Chicago Better for Families?

Orlando
Chicago

Kids will enjoy a visit to either Orlando or Chicago.

As it has a large number of activities for kids, Orlando is a very family-friendly destination. Known as a theme park capital, here you'll find the iconic Disney World, as well as Universal Studios, SeaWorld and many more.

Chicago is a very kid-friendly city. The city has a large number of activities for kids, including zoos, Shedd Aquarium, impressive children's museums, and large and elaborate playgrounds in Millennium Park.

Is Orlando or Chicago Better for Couples?

Orlando
Chicago

With fun activities for couples, both Orlando and Chicago make for a good place to visit.

Orlando is a nice destination for couples. While most people visit the area with family, there is a niche crowd that enjoys honeymooning or vacationing here as a couple. There are many beautiful restaurants and interesting activities that couples can enjoy together.

Chicago makes for a fun place to visit for a couple. Couples will enjoy exploring the city's vibrant theater scene and diverse neighborhoods.

Is Orlando or Chicago Better for Public Transit?

Orlando
Chicago

Chicago has better public transit to get you around.

Chicago has a great public transit system. There's a subway (the "L"), a commuter well, as well as buses and countless taxis available.

Public transit is generally limited in Orlando. If you're staying at a Disney Property, there is excellent transportation around the complex, but otherwise, a car is essential.

Is Orlando or Chicago a more walkable city?

Orlando
Chicago

Chicago is generally more walkable than Orlando.

Chicago is very walkable. The city has many restaurants, sights, and hotels that are easily accessible on foot.

Orlando is not a walkable city. The city is sprawling, so unless you stay on the Disney grounds, it's best to rent a car.


Should I spend more time in Chicago or Orlando?

How long in Orlando or Chicago?

In either Orlando or Chicago, you'll find plenty of activities to fill your time. Most visitors tend to spend more time in Chicago than Orlando because of the overall number of sights and activities.

The ideal length of time for a trip to Orlando is 7 days, and the ideal length of time for a trip to Chicago is 3-5 days.


  • How many days in Orlando or Chicago? Ideal Length of Stay
    Orlando 7 
    Chicago 3-5

One day in Orlando or Chicago?

In Orlando, you'll find nightlife and food. Travelers enjoy the resorts in the area as well. This city offers something for everyone. One day is usually not enough time for a trip here as there is plenty to do.

Because Chicago is a large city, there are a variety of ways to spend your time. This city offers something for everyone. One day is usually not enough time for a trip here as there is plenty to do.

A weekend in Orlando or Chicago?

In Orlando, you'll find food and shopping. The length of your trip often depends on your style of travel. People often spend their time relaxing at one of the resorts. Since there is so much to do in the area, a weekend is probably not enough for all of it.

Because Chicago is a large city, there are a variety of ways to spend your time. The length of your trip often depends on your style of travel. Since there is so much to do in the area, a weekend is probably not enough for all of it.

Five days in Orlando or Chicago?

Orlando is a great place to explore. You can also relax and pamper yourself at one of the resorts. Five days is more than enough time to enjoy everything. Take some day trips to nearby places to fill the extra days. Anyone can find something fun to do here.

Chicago is a great place to explore. It is common to spend five days here. Five days is a great amount of time to relax and see the many things that Chicago has to offer. Anyone can find something fun to do here.

A week in Orlando or Chicago?

It's hard to know how much time to spend in Orlando. Many people enjoy the theater and nightlife when visiting Orlando. It's also a relaxing resort destination. One week may feel like too much time unless you plan to do a lot of relaxing.

It's hard to know how much time to spend in Chicago. Many people enjoy the theater and nightlife when visiting Chicago. One week may feel like too much time unless you plan to do a lot of relaxing.

Which city is cheaper, Chicago or Orlando?

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

The average daily cost (per person) in Orlando is $255, while the average daily cost in Chicago is $221. 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 city. What follows is a categorical breakdown of travel costs for Orlando and Chicago in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Orlando $123
    Chicago $152
  • Accommodation Typical double-occupancy room
    Orlando $246
    Chicago $304
Compare Hotels in Orlando and Chicago

Looking for a hotel in Orlando or Chicago? 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 Orlando


Hotels in Chicago


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: Orlando Hotel Prices and Chicago Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Orlando $53
    Chicago $29
Typical Local Transportation prices in Orlando

Some typical examples of transportation costs in Orlando are as follows:


  • Parking
    $14
  • Taxi Ride
    $45

Hired Cars and Shuttles in Orlando

Also for Orlando, here are a few examples of actual transportation services:

  • Busch Gardens Shuttle Transfer: $299
  • Car Service Orlando International Airport Transfer To/From Hotel - One-Way: $128
  • Cruise Port of Orlando to Orlando Airport (MCO) - Departure Private Transfer: $80
  • Departure Private Transfer Orlando to Port Canaveral by Minibus: $186
  • Departure Private Transfer Orlando to Port Canaveral by SUV: $150
  • Disney World Resort to Cruise Port Canaveral. Private Transfer Up to 10 pax: $128
  • Disney World Resort to Cruise Port Canaveral. Private Transfer Up to 4 pax: $112
  • Disney World Resort to Orlando Airport MCO. Private Transfer Up to 10 pax: $58
  • Disney World Resort to Orlando Airport MCO. Private Transfer Up to 4 pax: $45
  • Disney World or Universal Studios transfer to Orlando Airport MCO up to 4 pax: $45
  • Disney World to Sanford International Airport (SFB) - Departure Private Transfer: $134
  • Disney/West 192 Hotels to Orlando Airport Private Transfer: $133

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:

  • Private Sedan Transfer between ORD and Indianapolis IN: $587
  • Private SUV Transfer Between O'Hare airport & Downtown Madison WI: $427
  • Private Sedan Transfer Between O'Hare airport & Downtown Madison WI: $426
  • Departure Private Transfer Chicago to O'Hare Airport ORD in a Minibus: $333
  • Arrival Private Transfer Chicago O'Hare Airport to Chicago City by Minibus: $333
  • Private SUV Transfer Between O'Hare airport & Downtown Milwaukee WI: $298
  • Transfer to Chicago Premium Outlets: $288
  • Private Sedan Transfer Between O'Hare airport & Downtown Milwaukee WI: $266
  • Chicago O'Hare Private Ground Airport/Hotel Transfer - Round-Trip: $256
  • Chicago Midway Airport/Hotel Round Trip Private Ground Transfer: $256
  • Chicago Midway Airport (MDW) to Chicago City - Round-Trip Private Transfer: $184
  • Chicago Airport Transfer by Private Sedan: $170

Is it cheaper to fly into Orlando or Chicago?

Prices for flights to both Chicago and Orlando 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
    Orlando $51
    Chicago $37
Typical Food prices in Orlando

Here are some examples of typical meal expenses from previous travelers to Orlando:


  • Lunch for Two at Epcot
    $29

Food Tours and Cooking Classes in Orlando

For Orlando, here are some samples of tours and activities related to meals and dining experiences:

  • The Outta Control Magic Comedy Dinner Show, Orlando: $34
  • Mango's Tropical Cafe Orlando Dinner and Show Ticket: $50
  • The Rock Dinner Show in Orlando: $51
  • Food Tour of Celebration: $55
  • Pirates Dinner Adventure Orlando: $57

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: $27
  • Learn to Make Chicago Deep-Dish Pizza with a Local: $49
  • Lonely Planet Experiences: River North Historical Food Tour: $61
  • Private Fusion Cooking Class in Downtown Chicago: $64
  • Best in Chow: Chicago River North Food Tour: $64
  • Signature Food Tour at Chicago's Navy Pier: $64
  • Skip the Line: Tommy Gun's Garage Dinner and Show Ticket: $67
  • Small-Group Chicago Food Tour: Gold Coast and Old Town: $75
  • Best of Chicago Tour Including a Deep-Dish Pizza: $75
  • River North Walking Food Tour: $75
  • Chicago's Wicker Park Food Tour: $75
  • Private Indian-Mexican Fusion Cooking Class with a Modern Cook: $78

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Orlando $163
    Chicago $34
Typical Entertainment prices in Orlando

For Orlando, here are some examples of average entertainment and activity prices from previous travelers:


  • Universal Studios for Two
    $110

Tours and Activities in Orlando

Also, here are some specific examples of entertainment, tickets, and activities for Orlando.

  • A Walk Around Lake Eola Audio Tour: $6.65
  • Port Canaveral Cruise shuttles: $15
  • Port Canaveral Cruise shuttles: $15
  • Factory Adventure Tour in Chocolate Kingdom: $18
  • Central Florida Zoo and Botanical Gardens Admission Ticket: $20
  • Orlando Walking Ghost Tour: $20
  • 1-Hour Haunted Walking Tour: $23
  • Titanic - The Artifact Exhibition Ticket: $24
  • Crayola Experience Orlando Ticket: $25
  • Lost Caverns Adventure Golf: $29
  • Skip the Line: Indoor Kart Racing Experience Ticket: $32
  • The Escape Game Epic 60-Minute Adventures: $37

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:

  • 2 Hours Chicago Sightseeing Tour - Luxury Private Stretch Limo / 8 Passengers: $250
  • 2-Hour Chicago City Lights and Skyline Segway Tour: $76
  • 2-Hour Chicago Fireworks Segway Tour: $76
  • 2-Hour Chicago Lakefront and Museum Campus Segway Tour: $73
  • 2-Hour Haunted Segway Tour of Chicago: $76
  • 2-Hour History of Chicago Architecture and Art Segway Tour: $75
  • 3 Hours Chicago Sightseeing Tour - Luxury Private SUV, ALL Inclusive: $392
  • 4 Hours Chicago Sightseeing Tour - Luxury Private SUV, ALL Inclusive: $220
  • 4 Hours Chicago Sightseeing Tour - Luxury Private Sedan: $215
  • 4 Hours Chicago Sightseeing Tour - Luxury Private Stretch Limousine/8 passengers: $728
  • A Most Magnificent Mile Shopping and Sightseeing Tour: $40
  • A Storied Neighborhood: Dance the dialectic with Bill Ayers on an audio tour: $5.00

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
    Orlando $24
    Chicago $20

Sample the Local Flavors in Orlando

Some specific costs for nightlife related activities in Orlando:

  • Florida Craft Beer & Brewery Tour: $65

Sample the Local Flavors in Chicago

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

  • Haunted Chicago Ghost and Pub Walking Tour: $25
  • Walking tour to Chicago dive bars: $41
  • Chicago Barrel Bus Craft Distillery Tour: $90
  • Chicago Craft Brewery Barrel Bus Tour: $90
  • Ultimate Girl's Night Out in Sparkling Wine, Photo Shoot, Burlesque: $900

About these numbers

When comparing the travel costs between Orlando and Chicago, we can see that Orlando is more expensive. However, the two cities are actually relatively comparable in price, as the difference is somewhat minimal. Generally, this means that you could travel with generally the same travel style and level of luxury in each place. Since both cities are in North America, it's no surprise that their costs are relatively close, as many destinations here have somewhat similar travel prices overall.


When is the best time to visit Orlando or Chicago?

Both places have a temperate climate with four distinct seasons. As both cities are in the northern hemisphere, summer is in July and winter is in January.

Should I visit Orlando or Chicago in the Summer?

The summer brings many poeple to Orlando as well as Chicago. The family-friendly experiences are the main draw to Orlando this time of year. Also, many travelers come to Chicago for the beaches, the city activities, the music scene, and the family-friendly experiences.

In July, Orlando is generally a little warmer than Chicago. Temperatures in Orlando average around 82°F (28°C), and Chicago stays around 77°F (25°C).

It's quite rainy in Chicago. Orlando receives a lot of rain in the summer. Orlando usually gets more rain in July than Chicago. Orlando gets 8.3 inches (211 mm) of rain, while Chicago receives 3.9 inches (100 mm) of rain this time of the year.


  • Summer Average Temperatures July
    Orlando 82°F (28°C) 
    Chicago 77°F (25°C)

Should I visit Orlando or Chicago in the Autumn?

Both Chicago and Orlando are popular destinations to visit in the autumn with plenty of activities. Many travelers come to Orlando for the shopping scene. Also, many visitors come to Chicago in the autumn for the city's sights and attractions, the shopping scene, the music scene, and the natural beauty of the area.

Orlando is much warmer than Chicago in the autumn. The temperature in Orlando is usually 75°F (24°C) in October, and Chicago stays around 56°F (14°C).

It's quite rainy in Orlando. In October, Orlando usually receives more rain than Chicago. Orlando gets 4.1 inches (103 mm) of rain, while Chicago receives 2.2 inches (56 mm) of rain each month for the autumn.


  • Autumn Average Temperatures October
    Orlando 75°F (24°C) 
    Chicago 56°F (14°C)

Should I visit Orlando or Chicago in the Winter?

Both Chicago and Orlando during the winter are popular places to visit. Many visitors come to Orlando in the winter for the Christmas ambience, the shopping scene, the theater shows, and the cuisine. Furthermore, most visitors come to Chicago for the museums, the Christmas ambience, the shopping scene, the theater shows, and the cuisine during these months.

Chicago can be very cold during winter. In the winter, Orlando is much warmer than Chicago. Typically, the winter temperatures in Orlando in January are around 59°F (15°C), and Chicago is about 25°F (-4°C).

Orlando usually gets more rain in January than Chicago. Orlando gets 2.3 inches (58 mm) of rain, while Chicago receives 1.9 inches (47 mm) of rain this time of the year.


  • Winter Average Temperatures January
    Orlando 59°F (15°C) 
    Chicago 25°F (-4°C)

Should I visit Orlando or Chicago in the Spring?

The spring attracts plenty of travelers to both Orlando and Chicago. Furthermore, the spring months attract visitors to Chicago because of the beaches, the activities around the city, and the natural beauty.

In April, Orlando is generally much warmer than Chicago. Temperatures in Orlando average around 72°F (22°C), and Chicago stays around 52°F (11°C).

Chicago receives a lot of rain in the spring. In April, Orlando usually receives less rain than Chicago. Orlando gets 2.7 inches (69 mm) of rain, while Chicago receives 4.3 inches (108 mm) of rain each month for the spring.


  • Spring Average Temperatures April
    Orlando 72°F (22°C) 
    Chicago 52°F (11°C)

Typical Weather for Chicago and Orlando

Orlando Chicago
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 59°F (15°C) 2.3 inches (58 mm) 25°F (-4°C) 1.9 inches (47 mm)
Feb 62°F (16°C) 3 inches (75 mm) 29°F (-2°C) 1.4 inches (35 mm)
Mar 67°F (19°C) 3.5 inches (88 mm) 41°F (5°C) 3.7 inches (93 mm)
Apr 72°F (22°C) 2.7 inches (69 mm) 52°F (11°C) 4.3 inches (108 mm)
May 77°F (25°C) 3 inches (75 mm) 63°F (17°C) 3 inches (75 mm)
Jun 81°F (27°C) 7.1 inches (181 mm) 73°F (23°C) 3.9 inches (100 mm)
Jul 82°F (28°C) 8.3 inches (211 mm) 77°F (25°C) 3.9 inches (100 mm)
Aug 82°F (28°C) 6.7 inches (171 mm) 76°F (24°C) 3.5 inches (90 mm)
Sep 81°F (27°C) 7.2 inches (183 mm) 68°F (20°C) 3.8 inches (96 mm)
Oct 75°F (24°C) 4.1 inches (103 mm) 56°F (14°C) 2.2 inches (56 mm)
Nov 68°F (20°C) 1.6 inches (40 mm) 44°F (7°C) 2.2 inches (56 mm)
Dec 62°F (17°C) 1.9 inches (48 mm) 31°F (-1°C) 2.8 inches (71 mm)


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