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Chicago Travel Itinerary Guide
Chicago Travel guide: It’s all here in Chicago — find out things to do, where to stay, when and where!`
Not Sure What To Do In Chicago?
Don’t worry. Let us guide you.
Panoramic image of the Cloud Gate or The Bean in the morning in Millennium Park, Chicago, Illinois
Known as the “Windy City,” Chicago is a world-class destination for culture, dining, architecture, sports and outdoor activities. Situated on the shores of Lake Michigan, Chicago’s downtown skyline is defined by iconic skyscrapers like Willis Tower, once the tallest building in the world. Visitors flock to top attractions like Navy Pier, Millennium Park, Art Institute of Chicago, Shedd Aquarium and the Museum of Science and Industry.
Baseball fans cheer on the Cubs at historic Wrigley Field, while foodies indulge in Chicago’s famous deep dish pizza. Chicago is also celebrated for its vibrant music scene, from jazz and blues to house music. Beyond the downtown Loop, Chicago has 77 distinct neighborhoods to explore. Food and art lovers browse Logan Square’s eclectic shops and Michelin-starred restaurants.
The Magnificent Mile features high-end shopping on North Michigan Avenue. Lincoln Park and Lakeview offer leafy green spaces close to the lakefront. Travelers can find boutique hotels in hip areas like Wicker Park and Andersonville.
From Millennium Park concerts in the summertime to Christmas lights along the Magnificent Mile, Chicago offers year-round activities. Whether you seek world-class museums, trendy bars, a vibrant LGBTQ scene, or lake cruises with skyline views, Chicago has something for everyone.
where to stay in Chicago?
Discover our top picks for Chicago hotels, a collection of our favorite hotels in Chicago that we’re excited to share with you. Each hotel in Chicago has been handpicked for a unique reason – whether it’s lavish amenities or unbeatable locations.
Ready to plan your Chicago vacation? Connect with our Chicago travel agency and get in touch with a travel artist who’s brimming with expert Chicago advice on making your journey truly memorable. Your dream vacation in Chicago awaits – let our savvy luxury travel advisors in Chicago be your guide to a memorable Chicago vacation.
If you’re looking for something different, use our exclusive partnership with booking.com to book hotels in Chicago on your own, or get in touch with us to handle all of your hotel bookings in Chicago for you! We are a full-service travel agency here to ensure your Chicago vacation is memorable!
Looking For Top Budget Friendly Hotels in Chicago?
Here are top 3 budget hotels as per Budget Traveler’s Choice.
Overlooking the Magnificent Mile on the bustling North Michigan Avenue, this 4-star Art Deco hotel in downtown Chicago is a 12-minute walk from the high-end shops and famous landmarks like the John Hancock Center, Water Tower Place, and Chicago Water Tower. With a prime location in the heart of the Windy City, guests can easily access top Chicago attractions like Cloud Gate sculpture in Millennium Park and the Navy Pier entertainment complex along Lake Michigan.
Situated along the scenic Chicago Riverwalk with views of the historic Michigan Avenue Bridge, this stylish Chicago boutique hotel is just steps from The Loop central business district and the Magnificent Mile shopping on North Michigan Avenue. Guests can take a relaxing stroll on the Chicago Riverwalk overlooking the Chicago River or explore popular Windy City attractions like Millennium Park, Art Institute of Chicago, Willis Tower, and the Chicago Theatre.
This convenient downtown Chicago hotel overlooks the scenic Chicago River and is located right on the Magnificent Mile shopping district, just north of the Chicago Loop in the heart of the city. Business travelers will appreciate being close to Chicago’s financial district and major companies while leisure guests can walk to iconic attractions like the Wrigley Building, Tribune Tower, Navy Pier, and Cloud Gate sculpture in Millennium Park.
Looking For Top Luxury Hotels in Chicago?
Here are top 3 budget hotels as per Luxury Traveler’s Choice.
Housed in the iconic AMA Plaza building designed by renowned architect Mies van der Rohe, this 5-star Magnificent Mile hotel overlooks the Chicago River and Lake Michigan showcasing sweeping views of the Chicago skyline. Steps from high-end shops and famous Chicago landmarks, this downtown hotel offers chic accommodations and amenities including a spa and indoor pool just minutes from Millennium Park, Art Institute of Chicago, Willis Tower, Water Tower Place, and the Chicago Theatre. The Langham is a Chicago hotels five star premier property.
Situated on exclusive North Michigan Avenue along Chicago’s famous Magnificent Mile shopping district, this 5-star Chicago hotel offers elegant rooms with sweeping city views in a prime location surrounded by luxury designer boutiques and acclaimed fine dining restaurants. Within walking distance of major Chicago attractions, guests can easily access Navy Pier, Oak Street Beach, the Museum of Contemporary Art, John Hancock Center, Millennium Park, and the Chicago Riverwalk.
Rising along Lake Michigan in Chicago’s exclusive Gold Coast neighborhood, this luxury Magnificent Mile hotel offers 5-star accommodations, Michelin-star dining, and an indoor pool with scenic city skyline views in the heart of downtown. Steps from high-end shops and restaurants, this contemporary Chicago hotel is surrounded by landmarks like the John Hancock Center, Water Tower Place, Tribune Tower, and the Museum of Contemporary Art.
where to eat in Chicago?
Uncover the best restaurants in Chicago. We have researched three of the best places to eat in Chicago. These made our list for a number of reasons: they could have delicious food in Chicago, be awesome Instagrammable restaurants in Chicago, or be a high-end restaurant in Chicago that can’t be missed!
Obviously, the culinary scene in Chicago is second-to-none, and we can’t include all restaurants in this list so if you want other restaurant recommendations in Chicago, contact one of our luxury travel artists (luxury travel advisors for Chicago) to help plan your full vacation itinerary in Chicago. We are a travel agency dedicated to providing memorable experiences in Chicago.
Top three Restaurants in Chicago: Journey Connected Expert’s Choice
Perched on the 16th floor of the iconic Chicago Athletic Association Hotel overlooking Millennium Park and Lake Michigan, this contemporary rooftop restaurant and bar offers stunning sweeping panoramic views of the Chicago skyline, Cloud Gate sculpture, and Maggie Daley Park. Guests can enjoy seasonal American cuisine, creative cocktails, and Chicago’s famous architecture against the backdrop of the city while relaxing on the outdoor terrace or in the light-filled dining room.
Located in Chicago’s edgy West Loop neighborhood, this trendy upscale cocktail lounge offers imaginative drink creations served in unique vessels like ice cubes, balloons, and more by expert bartenders. With an energetic and playful atmosphere, guests can watch skilled mixologists prepare tasty libations featuring uncommon ingredients and cutting-edge techniques at one of the most innovative bars in the Windy City. The menu changes seasonally, providing new cocktail adventures, including non-alcoholic options in a slick, stylish setting.
This fun, kitschy restaurant on North Wells Street transports guests back to a 1950s diner with its retro decor, antique memorabilia, and sassy waitstaff. Serving up classic American comfort foods like burgers, milkshakes, and fries, the menu features diner favorites prepared in heaping portions at this uniquely themed eatery. With a lively atmosphere and staff that interacts playfully with customers, dining at Ed Debevic’s offers a one-of-a-kind throwback experience in Chicago’s River North neighborhood.
what to see in Chicago?
Discover our top picks for city attractions and activities, a curated selection of our favorite experiences in city that we’re excited to share with you. Each one has been carefully chosen for its unique charm and cultural significance.
Ready to plan your city adventure? Connect with our experienced travel experts who are brimming with insider knowledge on making your journey truly unforgettable. Your dream vacation in city awaits – let our savvy city travel advisors be your guide to a memorable city holiday. As a trusted city Travel Agency, we’re here for you!
If you’re seeking something different, take advantage of our exclusive partnerships to book attractions and activities in city independently, or simply get in touch with us, and we’ll handle all of your city itinerary planning for you! These are the top five things to do in City. Use our travel concierge Chicago to book a custom Chicago itinerary for your next trip to Chicago!
top things to do in Chicago
Here are top three recommended activities by our travel experts
Chicago, Illinois
This 1 hour guided architecture cruise explores the Chicago River to view the city’s iconic skyscrapers and buildings. An expert guide provides commentary on over 40 notable structures along the river including the Willis Tower, Wrigley Building, Tribune Tower, Marina City and more. The tour sails along all three branches of the Chicago River for close up views of old and new architecture while learning about the history behind famous buildings. Major events like the Great Chicago Fire that shaped the city’s architectural landscape are also discussed. With unbeatable skyline views from the river vantage point, this is an excellent way to appreciate Chicago’s world-famous architecture.
from $48.78
Chicago, Illinois
This attraction provides visitors with panoramic views of Chicago from the 94th floor observatory of the John Hancock Center skyscraper. Ascend 1,030 feet up in under 40 seconds via North America’s fastest elevators. On the 360 Chicago observatory, guests can take in sprawling 360 degree views of famous landmarks like Willis Tower as well as Lake Michigan and the shoreline. Interactive exhibits provide details on Chicago’s architecture and history. The CloudBar offers drinks and light bites. Guests can upgrade onsite to include TILT – a thrilling ride that tilts visitors outwards for unique downward facing views. With stunning city vistas and fun activities, 360 Chicago delivers an exceptional overhead perspective of Chicago.
from $30.00
Chicago, Illinois
This attraction provides access to the observation deck on the 103rd floor of the Willis Tower in Chicago. Ascend 1,353 feet to the Skydeck in high-speed elevators for incredible 360 degree views of Chicago’s skyline and landmarks. Interactive exhibits detail facts about the tower and Chicago’s history. The highlight is walking on The Ledge, a glass balcony extending 4 feet outside the building with views down 1,353 feet. With a prepaid admission ticket, guests can skip main ticket lines for easy entry. For the best views, early morning and 30-45 minutes before sunset are ideal times to visit. The Skydeck offers a one-of-a-kind overhead perspective of Chicago from the tallest building in the western hemisphere.
from $44.00
Chicago, Illinois
The Chicago CityPASS is a discounted ticket booklet providing prepaid admission to 5 major Chicago attractions over a 9 day period. It includes unlimited access to Shedd Aquarium and Skydeck Chicago, plus your choice of 3 of these venues: Field Museum, Art Institute of Chicago, Museum of Science & Industry, 360 CHICAGO Observatory, Adler Planetarium, or an Architecture River Cruise. CityPASS allows visitors to experience Chicago’s top museums, observatories, and attractions at a discounted bundled rate while skipping most main-entrance ticket lines. With flexibility to visit venues on different days, it provides an easy and affordable way for families or travelers to maximize their time exploring Chicago’s famous sights.
from $139.00
Chicago, Illinois
This 2 hour lunch cruise aboard the Spirit of Chicago vessel offers incredible views of Chicago’s skyline while enjoying an all-you-can-eat buffet. The cruise sails along Lake Michigan past top attractions like Navy Pier, Soldier Field, and the skyscrapers of downtown. The buffet features a variety of salads, entrees like chicken and carved roast beef, desserts, and unlimited soft drinks. Live DJ entertainment creates a festive vibe with music and dancing. With amazing skyline perspectives, delicious food, and onboard fun, this cruise is ideal for families, groups and corporate outings.
from $88.84
You can book these things to do in Chicago from Journey Connected Travel Agency in Chicago, Illinois, browse all Viator Chicago attractions, or let one of our travel planners take care of the booking for you!
Chicago transportation
Chicago Ground Transportation and Chicago Airport Shuttle Service
Whether you need a ride to the Chicago airport or transportation after your flight, these are our recommendations for Chicago airport shuttle service and airport cars that provide convenient and reliable ground transportation in Chicago. These Chicago car services have drivers that will pick you and drive you directly to the airport terminal or hotel.
These are the best Chicago airport taxi and Uber services to get you to the airport in Chicago on time with no stress. These Chicago shuttle services and ‘transportation near me’ help avoid the hassle of parking and expensive parking fees; book these Chicago airport shuttle service in advance. Contact us today to schedule Chicago airport shuttle near you and relax on your next trip or click the links below to book on your Chicago airport transfers on your own.
plan a Chicago vacation
Help Planning A Vacation to Chicago With A Top Chicago Travel Agency
Journey Connected proudly presents a free three-day Chicago travel guide, meticulously curated to showcase the finest attractions in Chicago and the best Chicago experiences. Unveil the magic of one of the world’s most visited cities, exploring top landmarks in Chicago and delving into hidden gems. Indulge in the Chicago culinary scene with recommendations for the best restaurants in Chicago, enhancing your journey through this enchanting destination.
From Chicago in the summer to the festive allure of Chicago in the winter, this guide captures Chicago seasonal delights. Embark on a seamless adventure in one of the best cities to visit in the world, leaving no top things to see and do in Chicago unexplored. Your vacation to Chicago awaits – an epitome of the best places to visit in the world. Use our Chicago travel guide or contact our luxury travel agency Chicago, and let us plan your next Chicago vacation!
Download our travel guide for planning a trip to Chicago.
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Chicago travel blogs
Enjoy our Chicago Travel Blogs Full of Chicago Travel Information
Our Chicago travel blogs offer insider tips, inspiring stories, and helpful Chicago advice to make your next vacation in Chicago the best one yet. Written by our team of passionate Chicago travel experts, our blogs cover a range of information about traveling in Chicago and must-do activities in Chicago. You’ll discover new places to explore in Chicago and learn insider secrets about old favorites.
Our travel writers and Chicago travel advisors provide detailed Chicago guides with Chicago recommendations on where to stay, what to do, where to eat, and how to get around in Chicago. Whether you are an expert on Chicago or just starting to plan your vacation to Chicago, let our travel guides and blogs be a partner to you. You’ll find engaging articles, beautiful Chicago photos, and practical information in our collection of fun and informative travel blogs. Reading our Chicago blogs is the next best thing to being there yourself!
When you’re ready to plan your Chicago vacation, contact one of our expert Chicago travel advisors and let Journey Connected travel agency provide you a custom Chicago travel itinerary for your vacation!
Chicago FAQs
Frequently Asked Questions about Chicago
Chicago, Illinois, is best known for its stunning architecture, deep-dish pizza, and vibrant cultural scene. The city is famous for landmarks like the Willis Tower (formerly Sears Tower), Navy Pier, and the Chicago Riverwalk, as well as its iconic skyline featuring the works of architectural pioneers.
It’s also a hub for art, music, and theater, with institutions like the Art Institute of Chicago, the Chicago Symphony Orchestra, and a thriving live comedy scene, including the renowned Second City.
Chicago’s culinary reputation is highlighted by its signature deep-dish pizza, Chicago-style hot dogs, and a wide variety of Michelin-starred restaurants. Additionally, the city’s sports culture is strong, with teams like the Chicago Cubs, Bulls, and Bears having passionate fanbases.
Journey Connected can help you explore the best of Chicago, from its world-class attractions to its food and entertainment, ensuring a memorable visit to the Windy City.
Spending 3 to 4 days in Chicago is typically enough to explore the city’s major attractions and get a taste of its vibrant culture. Here’s a suggested breakdown:
Day 1: Visit downtown highlights like the Willis Tower Skydeck, Millennium Park (home of the iconic Cloud Gate, or “The Bean”), and stroll along the Chicago Riverwalk.
Day 2: Dive into Chicago’s rich culture with a visit to the Art Institute of Chicago or the Field Museum, and spend time at Navy Pier for stunning lake views, dining, and entertainment.
Day 3: Explore unique neighborhoods like Wicker Park or Lincoln Park, and sample Chicago’s famous deep-dish pizza and other local cuisine. If time allows, catch a game at Wrigley Field or enjoy the nightlife in the West Loop.
Day 4 (optional): Take a scenic architecture boat tour, visit the Museum of Science and Industry, or relax with some shopping along the Magnificent Mile.
Journey Connected can help you plan a custom Chicago itinerary to make the most of your trip, whether you’re in town for a weekend or an extended stay.
Yes, Chicago is a very walkable city, especially in its downtown area and popular neighborhoods. Many of the city’s top attractions, like Millennium Park, the Art Institute of Chicago, and the Chicago Riverwalk, are within close proximity and can be easily explored on foot. The layout of the city, with its grid-like streets and clearly marked signs, makes navigation simple for visitors.
Neighborhoods like The Loop, River North, and Lincoln Park are pedestrian-friendly, with plenty of shops, restaurants, and parks to enjoy as you stroll. Additionally, the scenic Lakefront Trail, stretching 18 miles along Lake Michigan, is perfect for walking, running, or biking while taking in beautiful views of the city and lake.
While walking is ideal for exploring many parts of Chicago, the city’s extensive public transportation system, including buses and the “L” trains, makes it easy to reach farther attractions like Wrigley Field or the Museum of Science and Industry.
Journey Connected can help you design a walking-friendly itinerary to ensure you experience the best of Chicago’s charm, landmarks, and vibrant neighborhoods.
Chicago and New York are both iconic U.S. cities, but they offer distinct experiences that cater to different preferences. Here’s how they compare across key aspects:
Size and Pace
- New York City is larger and more fast-paced, with a population over 8 million and a 24/7 hustle-and-bustle vibe. It’s a global financial and cultural hub with endless activity.
- Chicago is smaller and more manageable, with about 2.7 million residents. It offers a dynamic urban experience but at a more relaxed pace compared to NYC.
Architecture and Landmarks
- Chicago is renowned for its architecture and skyline, home to the Willis Tower, the John Hancock Center, and the Chicago Riverwalk, as well as a strong architectural history influenced by Frank Lloyd Wright.
- NYC’s skyline is iconic, featuring landmarks like the Empire State Building, One World Trade Center, and Statue of Liberty. Its dense urban layout makes it the ultimate vertical city.
Culture and Arts
- Both cities have rich cultural scenes, but New York is unparalleled in its sheer volume of museums, Broadway theaters, and global arts institutions like the Metropolitan Museum of Art and the MoMA.
- Chicago excels in live music (notably jazz and blues), comedy (The Second City), and world-class museums like the Art Institute of Chicago and the Field Museum.
Food
- New York is known for its diverse cuisine, with iconic foods like pizza slices, bagels, and an endless variety of international options.
- Chicago is famous for deep-dish pizza, Chicago-style hot dogs, and an emerging fine-dining scene with Michelin-starred restaurants.
Cost of Visiting
- Chicago is generally more affordable for accommodations, dining, and attractions, making it an excellent value for travelers.
- NYC tends to be more expensive in nearly every category, from hotels to transportation.
Public Transportation
- NYC’s subway system is extensive, running 24/7 and making it easy to get anywhere in the city.
- Chicago’s “L” trains are also convenient and reliable, though the system is smaller compared to New York’s subway network.
Vibe and Atmosphere
- NYC offers a high-energy, non-stop urban experience with a global, multicultural flair.
- Chicago provides a mix of big-city excitement and Midwestern friendliness, with a focus on local charm and outdoor spaces like the Lakefront Trail and Millennium Park.
Ultimately, the choice between Chicago and New York depends on what kind of trip you’re looking for. Journey Connected can help you plan the perfect itinerary for either destination, ensuring you enjoy the unique highlights of each city!
Washington, DC, is generally more expensive than Chicago, but the difference can vary depending on what aspects of travel or living you’re comparing. Here’s a breakdown:
Accommodations
- DC: Hotels and accommodations in Washington, DC, tend to be pricier, especially near major attractions like the National Mall. Budget options are available, but they may require staying in surrounding areas.
- Chicago: While Chicago has luxury hotels, it generally offers more affordable accommodations, especially if you stay outside of downtown or during the off-season.
Dining
- DC: Dining in DC can be expensive, particularly in trendy neighborhoods or near government areas. Upscale dining and fine restaurants are common.
- Chicago: Chicago offers a wide range of dining options, from budget-friendly spots like local deep-dish pizza joints to high-end Michelin-starred restaurants. Overall, Chicago dining tends to be more affordable.
Transportation
- DC: Public transportation is efficient but slightly pricier. Parking in the city is also costly and limited.
- Chicago: The “L” train and bus systems are slightly cheaper than DC’s Metro. Parking can also be expensive, particularly downtown.
Attractions
- DC: Many major attractions, like the Smithsonian museums and monuments, are free to visit, which can significantly cut costs.
- Chicago: Attractions like the Skydeck, the Art Institute, and boat tours typically have entrance fees, but the city also offers free options like Millennium Park and Navy Pier.
Overall Cost
- Housing and living expenses: If comparing the cost of living, DC is consistently ranked as more expensive than Chicago in terms of rent, utilities, and daily expenses.
- Travel and vacation costs: Chicago may be slightly more affordable overall, especially if you’re budget-conscious.
If you’re planning a trip, Journey Connected can help you find affordable options in either city, tailoring your itinerary to your budget while ensuring you enjoy the highlights of Washington, DC, or Chicago.
Are you tired of travel plans that don’t live up to your dreams?
Elevate your next journey with expert vacation planning that turns every trip into an unforgettable adventure! Stop wasting time and money—trust our professionals to book your travel and create the perfect, personalized itinerary just for you.
Tired of travel plans that fall short?
Elevate your journey with expert, personalized vacation planning for an unforgettable adventure.
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