Chicago Travel Itinerary – Top Things to Do in Chicago | Where to Stay in Chicago | Chicago Travel Agency | Planning a Vacation to Chicago
Plan a vacation with a tour and travel agency to Chicago!
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.
Book the best Chicago hotels on your own, browse thousands of the top hotels in Chicago on booking.com using the search box below. Find budget hotels in Chicago or five star hotels in Chicago:
Three Perfect Days in Chicago | Help Planning A Vacation to Chicago
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 Chicago travel guide for planning a trip to Chicago, or scroll to the bottom of this page to view it
Top Hotels 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 in five star hotels Chicago in luxury hotel rooms Chicago 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! Get five star hotel Chicago recommendations here!
Budget Friendly Hotels in Chicago
Warwick Allerton Chicago - 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.
River Hotel - 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.
Club Quarters Hotel Wacker at Michigan - 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.
Luxury 5 Star Hotels in Chicago
The Langham Chicago - 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.
The Peninsula Chicago - 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.
Four Seasons Hotel Chicago - 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.
Top Restaurants 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.
Cindy's - 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.
The Aviary - 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.
Ed Debevic's - 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.
Enjoy our Chicago Travel Blogs Full of Chicago Travel and Concierge 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 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.
Top Activities in Chicago
Discover our top picks for Chicago attractions and activities, a curated selection of our favorite experiences in Chicago that we're excited to share with you. Each one has been carefully chosen for its unique charm, cultural significance, or fun activities in Chicago. Ready to plan your Chicago vacation? Connect with our experienced travel experts who are eager to plan your Chicago vacation. Your dream vacation in Chicago awaits – let our savvy Chicago travel advisors be your guide to a memorable Chicago holiday. As a trusted Chicago Travel Agency, we’re here for you! If you're seeking something different, take advantage of our exclusive Chicago partnerships to book attractions and activities in Chicago independently, or simply get in touch with us, and we'll handle all of your Chicago itinerary planning for you! These are the top five things to do in Chicago.
Chicago Architecture River Cruise - 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.
360 CHICAGO Observation Deck Admission (Hancock Center) - 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.
Skydeck Chicago Admission Ticket - 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.
Chicago CityPASS - 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.
Big Bus Chicago Hop-On Hop-Off Tour - This hop-on hop-off bus tour allows passengers to explore Chicago's top attractions at their own pace. An open-top, double-decker bus makes a loop with stops at famous sights such as Millennium Park, Art Institute of Chicago, Willis Tower, Grant Park and more. Audio commentary provides background on the sights throughout the tour. Buses run on various schedules so passengers can hop-on and hop-off as often as they like to visit different attractions. Classic, Premium and Deluxe tickets are available to suit different schedules. With route planning handled by the tour, visitors can easily see Chicago's highlights without navigating public transportation.
Chicago Buffet Lunch Cruise on Lake Michigan - 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.