Chicago Travel Guide
Fly Like a Super Pig to Any One of the below page Sections:
Top Attractions
Cheap Flying Tips
Where to Stay
Things to Do
Your Guide to Chicago
Chicago is one of the United States’ most rich and vibrant cities. Currently sitting as the third most populous city in the US, Chicago boasts wonderful shopping, eateries, and cultural wonders as well as adventures and views to keep everyone entertained.
There are many attractions to visit and tips for visiting Chicago that will make your trip enjoyable. Read on to discover these suggestions and make the most of your trip to the Windy City!
Top Attractions in Chicago
There are hundreds of wonderful attractions to choose from in Chicago. Luckily, there are a few standouts that are distinguished from the rest. These include:
- Millennium Park
- Magnificent Mile and Navy Pier
- Chicago River Cruise
Millennium Park
Millennium Park offers a wide variety of free public entertainment. This is where the iconic, reflective metal “Bean” is located, as well as several stages for live music and other forms of entertainment.
Other options at Millennium Park include:
- Film screenings
- Botanical gardens
- Food stands
- Live music
Spread a blanket on the grass and enjoy a picnic under the sun or walk among the stands and shops surrounding the park.
Throughout the summer months, many nonprofits set up day camps for kids of various age groups.
Millennium Park is free to visit and easily accessible via public transportation.
Magnificent Mile and Navy Pier
The Magnificent Mile is almost synonymous with Chicago itself. This is a shopping district along Michigan Avenue that spans 13 city blocks.
It is centrally located near downtown and contains many attractions, including:
- High-end shops
- Eateries
- Historic landmarks
- Scenic views
A mile further lies Navy Pier, a continuation of the lively Magnificent Mile. Here there are many fun attractions, including the Centennial Wheel, a 200-foot tall wheel with enclosed gondolas that offer 360-degree views of the city.
Also found on Navy Pier are various tours and sightseeing options, like river cruises and historic landmark tours of the city.
Chicago River Cruise
The Chicago River Cruise is a fun tour for all ages. This sightseeing tour takes visitors along Michigan Avenue for an hour. You will see (and learn about) most of Chicago’s major architectural wonders, including:
- Wrigley Building
- Navy Pier
- Willis Tower
- Tribune Tower
- The Lyric Opera House
- 360 Chicago Observation Deck
This river cruise departs from Navy Pier and has multiple slots available to fit your schedule. It is recommended to book early, as this tour often sells out!
The unique views of the Chicago Skyline from along the river are unmatched, and the local guide will have heaps of information to share.
The Experience Flying into the Chicago Airport
The Chicago O’Hare International Airport is one of the busiest airports in the country, taking the top spot in 2019. It consistently ranks within the Top Ten busiest airports in the world.
O’Hare houses many local Chicago eateries and contains many shops and amenities for the everyday traveler. Find a souvenir, post-flight snack, or visit the spa to de-stress before jumping into the city’s high energy and numerous attractions.
With nearly 2,500 flights daily through the Chicago O’Hare International Airport, there are plenty of options for anyone, anywhere, to make it to Chicago cheaply and efficiently.
Below we will discuss several tips and tricks to travel to Chicago on a budget.
With eight terminals, over 300 gates, and an average of 150,000 passengers per day, this building’s mammoth might be a bit overwhelming and difficult to navigate. The best plan of action would be to use the 24/7 airport rail,AirTrain, to travel between terminals.
However, before you rush out into the bustle of New York City, take a moment to appreciate some of the exceptional services JFK has to offer. Shop around in Terminal 5, grab a bite to eat at Terminal 4, or get pampered at one of the spas in Terminals 1, 4, and 7. Once you’re well-fed and refreshed, you’ll be ready to take on The Big Apple.
Top 3 Tips to Fly Cheap to Chicago
There are several ways to reduce travel costs when flying to Chicago. These include:
- Booking your travel early
- Booking your tickets early in the week
- Traveling in the off-season
1. Booking your travel early
First, book your travel early. Planning ahead is a great way to save money on flights to Chicago.
Booking tickets as early as three to five months in advance can save you hundreds of dollars. Waiting to book until a few weeks before departure can rack up additional fees and costs.
SkyScanner reports that tickets booked to Chicago 3 months in advance were nearly $350 less than tickets booked a week before departure.
2. Booking your tickets early in the week
Second, book your tickets early in the week. These have cheaper prices on average, specifically savings increases when booking around midnight on Monday, Tuesday, or Wednesday. Booking your tickets to be flying on a Tuesday, Wednesday or Saturday will often also lower the price.
3. Traveling in the off-season
Finally, if possible, travel to Chicago in the off-season. January and February are the cheapest months to fly into Chicago. Avoid June and July, where flights are nearly 14% more expensive than throughout the rest of the year.
Popular Areas of the City to Stay
After buying your plane tickets, the next step is to figure out where you’ll stay. Some of the most popular areas of New York City are:
Depending on your reason for visiting Chicago, the best area of the city to stay will vary.
Some travelers visit Chicago for a lively family vacation, some business-minded individuals prefer to relax in luxury, and others are searching for budget-friendly accommodation for their stay.
With nearly 100 defined neighborhoods in Chicago’s city limits, there is sure to be a location that fits your needs.
Some of the best areas to stay during a family vacation include:
- Lincoln Park neighborhood
- River North neighborhood
Some of Chicago’s most luxurious accommodations can be found on:
- The Magnificent Mile
- Gold Coast neighborhood
For a budget-friendly value during your stay, look to book in these areas:
- Grant Park neighborhood
- Magnificent Mile
Popular Hotels in Those Areas
For the family-friendly bunch, hotels in the Lincoln Park and River North neighborhood are a good choice. These areas are centrally located with many enticing amenities for kids and adults alike. Some of the highly recommended hotels in these areas include:
Luxurious accommodations in the Gold Coast neighborhood and Magnificent Mile are some of the most popular choices for celebrities, professional athletes, and travelers looking for the highest quality amenities. Some of these choice hotels include:
Other travelers are searching for quality, comfortable accommodation that won’t stretch their budget. The Grant Park neighborhood is a wonderful choice, although there are more budget-conscious hotels along the Magnificent Mile for travelers looking to be closer to the action. Some hotels in this area include:
No matter the desired accommodations, Chicago has a hotel for anyone. For others who aren’t interested in booking hotel rooms, Airbnb is a wonderful option.
Popular VRBO Places in those Areas
Magnificent Mile Penthouse
Enjoy breathtaking city views from this luxurious penthouse situated on the Magnificent Mile. Featuring upscale amenities, contemporary design, and easy access to Chicago’s top attractions, this rental offers an unforgettable stay.
Historic Brownstone Getaway
Experience Chicago’s charm in this beautifully restored brownstone, located in the trendy Wicker Park neighborhood. With elegant interiors and a private garden, this classic home promises a memorable stay.
Lakefront Luxury Condo
Wake up to serene lake views in this modern, high-rise condo. Boasting floor-to-ceiling windows, sleek design, and a prime location near the city’s top attractions, this rental is perfect for exploring the Windy City.
Cozy Lincoln Park Cottage
Discover a peaceful retreat in this charming Lincoln Park cottage. Surrounded by lush gardens, this cozy home offers a serene escape from the city while remaining close to top dining, shopping, and entertainment options.
Top Things to Do in Chicago
The Chicago CityPASS is an affordable and efficient way to visit many of the top attractions in Chicago. For a flat rate of $109 for adults and $89 for children, you are granted access to your choice of 5 attractions to visit within nine consecutive days.
The CityPASS also often includes coupons for souvenirs, other attractions and sometimes offers the ability to skip-the-line at the busier attractions.
Right now, the Chicago CityPASS includes admission to the following:
- Shedd Aquarium
- Skydeck Chicago
- Field Museum
- Adler Planetarium or Art Institute of Chicago
- Museum of Science and Industry or 360 Chicago Observation Deck
Each of these attractions has its own individual merits, and any visitor, whether it be for family vacation or business, is sure to enjoy these experiences.
The Shedd Aquarium
The Shedd is for nature lovers. With over 5 million gallons of aquatic displays to explore, this indoor aquarium contains over 1,500 species ranging from reef sharks to seahorses. Their penguin named Wellington was just chosen as “Chicagoan of the Year” for 2020!
CityPASS includes general admission and admission to permanent exhibits. It also includes access to various rotating animal presentations and special exhibits, including a 4-D experience and Stingray Touch.
Skydeck Chicago
The Skydeck is not for the faint of heart. Located on the 103rd floor of the Willis Tower (previously Sears Tower), this glass box known as the “SkyDeck” sticks out over 4 feet from the side of the building. Standing in a human-sized, square fishbowl, the views of the city are imaginably incredible.
CityPASS includes expedited admission to the tower (103rd floor) and onto the ledge.
The Field Museum of Chicago
Also known as the Field Museum of Natural History, this is one of the largest natural history museums in the world. It contains numerous exhibits and collections, such as:
- Ancient Egypt
- Herpetological Library
- Gems and Fossils
- Animal Halls
- Evolving Planet
- Dinosaurs
The museum also offers many rotating exhibits across numerous topics throughout the year. Be sure to check in and plan your visit; accordingly, it’s difficult to see everything you want to see in just one visit!
CityPASS admission includes VIP entry and admission to all exhibits. It also includes your choice of one 3D film.
The Adler Planetarium
Chicago’s planetarium is an exciting look into the known-universe and astronomy. With several rotating exhibits and tours, there is sure to be something for everyone. Hands-on activities, space shows, and a giant telescope are just a few of the major draws.
CityPASS includes general admission and access to all permanent and temporary exhibits. It also includes your choice of two sky shows during your visit.
Art Institute of Chicago
There is a reason the Art Institute ranks at #1 for Chicago’s most popular museums. Just a few of their many current exhibitions include:
- Monet and Chicago
- Jewelry of South Asia’s Nomadic Cultures
- Medieval and Renaissance Art, Arms, and Armor
CityPASS admission includes fast pass admission and access to all regular and special exhibits.
Chicago's Museum of Science and Industry
This is the largest science center in the western hemisphere. Here you can find full-sized replicas of:
- A coal mine
- A German submarine
- Model of Apollo-8
- First diesel-powered passenger train
The MSI contains over 2,000 exhibits spread across dozens of halls, ranging from a mirror maze to a video game exhibit to a Titanic replica collection. No matter your area of interest, there is sure to be several interesting finds.
CityPASS admission includes museum entry and admission to all exhibits, including:
- Science Storms
- Numbers in Nature: A Mirror Maze
- YOU! The Experience
It also includes a timed-entry experience to one of the following:
- Giant Dome Theater film
- Coal Mine tour
- Fab Lab
- Wired to Wear
Chicago Observation Deck
This is located at the top of the John Hancock Center, nearly 1,000 feet above the magnificent mile. For the more daring traveler, there is the option to ride the “Tilt Deck,” one of the highest thrills rides on the planet.
Visitors hold vertical handrails while facing a glass wall overlooking the city. The wall then tilts outward, offering downward views of the city.
CityPASS admission includes express entry admission.
Coolest Airbnb Experiences in Chicago
Along with booking AirBNB accommodations for staying in Chicago, Airbnb also offers a multitude of experiences that can be booked with their services, much like TripAdvisor. Chicago is rich in experiences, and AirBNB offerings are no different. These experiences include:
- Bike tour of Chicago
- Flight Lessons
- CHI-TOWN SHOWDOWN Scavenger Hunt
- Food Tour (tapas, bikes & brews, vegan, etc.)
- Photo Shoot (lifestyle, cityscape, etc.)
- Gangsters & Ghosts Tour
These Airbnb offerings, among many others in Chicago, are sure to please any traveler.
Enjoy the Windy City’s Wonders
Chicago’s unique and one-of-a-kind experiences are not to be missed. Whether you are interested in history, architecture, art, cityscapes, the animal kingdom, or simply craving a world-famous slice of deep-dish pizza, Chicago is the city to visit.
