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Chicago Vacation Packages 2025/2026 from $623 | Expedia

Chicago offers a vibrant mix of family-friendly activities and outdoor adventures, making it perfect for a city-themed vacation. Visitors can explore popular shopping districts, enjoy thrilling sporting experiences, and visit iconic attractions. Don't miss out on free outdoor attractions that ... With a multitude of well-known landmarks and vibrant neighborhoods to explore, Chicago promises an unforgettable vacation. Discover accommodations in downtown Chicago, offering access to top-tier dining, cultural hotspots, and captivating entertainment.Chicago offers a vibrant mix of family-friendly activities and outdoor adventures, making it perfect for a city-themed vacation. Visitors can explore popular shopping districts, enjoy thrilling sporting experiences, and visit iconic attractions. Don't miss out on free outdoor attractions that highlight the city's charm.Visitors can immerse themselves in the city's rich culture while exploring iconic attractions like the Chicago River and the scenic Riverwalk. Whether you're looking for a city-themed vacation or a family-friendly experience, Chicago has something to offer everyone.You'll find cheap prices from $342 on Expedia for your Chicago escape. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Chicago costs.

Chicago, IL: All You Must Know Before You Go (2025) - Tripadvisor

Chicago Tourism: Tripadvisor has 1,144,566 reviews of Chicago Hotels, Attractions, and Restaurants making it your best Chicago resource. Aloft (Marriott Bonvoy) Hotels in ChicagoHilton Hotels in ChicagoAccor Hotels in ChicagoWyndham Hotels in ChicagoChoice Hotels in ChicagoWestin (Marriott Bonvoy) Hotels in ChicagoRenaissance Hotels (Marriott Bonvoy) in ChicagoHoliday Inns in ChicagoCourtyard (Marriott Bonvoy) Hotels in ChicagoRodeway Inns in ChicagoHyatt Hotels in ChicagoHyatt House Hotels in ChicagoTribute Portfolio (Marriott Bonvoy) Hotels in ChicagoHyatt Regency Hotels in ChicagoHome2 Suites by Hilton in ChicagoPopular AmenitiesChicago MotelsChicago HostelsChicago Family HotelsRomantic Hotels in ChicagoChicago Spa ResortsChicago ResortsChicago Business HotelsChicago Green HotelsChicago Luxury HotelsChicago Beach HotelsBy Hotel ClassChicago TourismChicago HotelsChicago Bed and BreakfastFlights to ChicagoChicago RestaurantsThings to Do in ChicagoChicago Travel ForumChicago PhotosChicago MapHotelsAll Chicago HotelsChicago Hotel DealsLast Minute Hotels in ChicagoHotels Near MeBy Hotel Type

The Best Weekend Getaways From Chicago for Beaches, Museums, and More

The best weekend destinations close to Chicago require no flights. Here's where to go within three hours of Chicago. Despite cries about that winter weather, Chicago is inarguably blessed with a little something we like to call location, location, location: There are more than half a dozen appealing cities under three hours from Chicago by car, including Milwaukee and its famed brews and brats, plus a handful of destinations that you can reach by train.OK, OK. Geneva is technically a suburb of Chicago, but it feels worlds away, thanks to its small-town charm. Drop your bags at the boutique Herrington Inn & Spa, located on the Fox River. Five minutes’ drive from the hotel is the peaceful Fabyan Japanese Garden; although it’s open May 3 through September 28 only, this is enough time to see spring flowers and colorful fall foliage.On a clear day in Michigan City, you can see Chicago’s skyline across the water. Enjoy towering sand dunes, the cool waters of Lake Michigan, and nearly 50 miles of trails at Indiana Dunes National Park, less than 10 minutes’ drive from the town center.Of course, there’s plenty to do in Chicago before you head off; it was ranked number two in the best U.S. cities in 2024, after all, thanks to its top restaurants, world-class museums, and abundant hotel options. It’s also remarkably kid-friendly.

Chicago Travel Guide - Vacation & Trip Ideas

Visit Chicago for an unforgettable adventure. Discover the best hotels, restaurants and things to do with this highly curated Chicago travel guide. The park is often called "Chicago's front yard" and includes the Art Institute of Chicago, Millennium Park, and the iconic Buckingham Fountain, which was featured in the title sequence of the TV show "Married... with Children" and the movie "National Lampoon's Vacation".Chicago is home to more than 2.7 million people, making it the third largest city in the U.S. and the largest city in the midwest. It's lined with urban beaches located along Lake Michigan and is known as the birthplace of the modern skyscraper.Chicago isn't just about sports, though. It's also a foodie paradise with world-class museums, architectural gems, luxury shopping, and a long list of live music venues and comedy clubs. It's a place where you're sure to find plenty of things to do — and eat.Chicago may have freezing winters, but the Windy City makes up for it with warm, sunny summer days filled with live music, neighborhood festivals, and bright blue skies. The best time to visit Chicago is between June and September when the city's urban beaches are at their best.

Chicago Getaway | Amtrak Vacations®

Discover all the “Windy City” has to offer on this Chicago Getaway. Explore the Magnificent Mile, listen to great music at an amazing blues club, & more. Discover all options for customizing your rail vacation!See a rail vacation package you like, but it would be even better with an extra day at the beginning or end of the journey? Or an extra day in between in a different destination?

Ideas for One Epic Day Trip to Chicago in 2025

Morning: Explore the Lincoln Park ... free Chicago family attractions. Don’t miss the Farm-in-the-Zoo for hands-on animal encounters. Afternoon: Visit the Peggy Notebaert Nature Museum—its butterfly haven is a magical experience for kids. Evening: Picnic at North Avenue Beach for a scenic and relaxed end to the trip. Perfect for a family vacation in Chicago ... Morning: Explore the Lincoln Park Zoo, one of the best free Chicago family attractions. Don’t miss the Farm-in-the-Zoo for hands-on animal encounters. Afternoon: Visit the Peggy Notebaert Nature Museum—its butterfly haven is a magical experience for kids. Evening: Picnic at North Avenue Beach for a scenic and relaxed end to the trip. Perfect for a family vacation in Chicago on a budget or a mix of fun things for families to do in downtown Chicago with engaging, educational stops.Planning a Chicago vacation with family can feel overwhelming with so many family-friendly activities in Chicago to choose from.Whether you’re with family, friends, or on a solo adventure, Chicago is full of activities that cater to every interest and age group. Here’s a guide to some of the best day trip ideas in Chicago, perfect for everyone from first-time visitors to seasoned Chicagoans.Whether you’re here for a family outing, a day with friends, or a solo adventure, Chicago’s energy is infectious. From sunrise walks along the lakefront to sunset views from a rooftop bar, this city offers a mix of history, architecture, art, food, and just enough quirk to keep you coming back.

Chicago Holidays 2025 / 2026 from £576 | Cheap Holidays to Chicago | lastminute.com

Booking a flight + hotel package to Chicago with lastminute.com offers several advantages. By booking both services together, you can take advantage of exclusive deals and choose from thousands of flights and accommodations for the perfect combination. Additionally, you can secure your vacation ... Booking a flight + hotel package to Chicago with lastminute.com offers several advantages. By booking both services together, you can take advantage of exclusive deals and choose from thousands of flights and accommodations for the perfect combination. Additionally, you can secure your vacation with a deposit and pay the remaining amount later.Find the best deals on Chicago holidays from £576 at lastminute.com. Book with a small deposit and pay the rest later. ATOL protected.Embrace the spirit of Americana and jet off for a holiday to Chicago, a dynamic city that offers experiences you won't soon forget. Unearth the history and culture of the "Windy City," from iconic Route 66 to its globally celebrated blues music. How about dining atop a skyscraper overlooking skylines as you indulge in the city’s legendary deep dish pizza?This city within a park, with its vast green spaces like Millennium Park, beckons you for some leisure time. In Chicago, every sports enthusiast finds joy, whether it's cheering with locals at a Cubs game or exploring the United Center, home to the Bulls and the Blackhawks.

Chicago Vacation Packages & Travel Deals | Vacations by Marriott Bonvoy

Yes, Vacations by Marriott Bonvoy offers flight and hotel packages to Chicago, Illinois—a dynamic city known for its iconic skyline, deep-dish pizza, and world-class museums. These bundled vacation deals allow you to book both airfare and accommodations in one seamless transaction, often ... Experience the charm and energy of the Windy City with Chicago vacation packages from Vacations by Marriott Bonvoy. Visit iconic landmarks like Millennium Park and Navy Pier, enjoy world-class dining, and explore vibrant neighborhoods. With luxurious accommodations and endless activities, Chicago is the perfect destination for your next getaway.Experience more and spend less with Vacations by Marriott Bonvoy. ... Chicago is a vibrant city with a wealth of attractions to explore. Millennium Park is a must-see, featuring the iconic Cloud Gate sculpture, often referred to as "The Bean," and the stunning Jay Pritzker Pavilion.Another Chicago staple is the Chicago-style hot dog, an all-beef frankfurter served on a poppy seed bun and topped with mustard, onions, relish, tomatoes, pickles, sport peppers, and a dash of celery salt—no ketchup allowed! For a sweet treat, don’t miss Garrett Popcorn, known for its addictive Chicago Mix of caramel and cheese popcorn. Does Vacations by Marriott Bonvoy offer flight and hotel deals to Chicago?Yes, Vacations by Marriott Bonvoy offers flight and hotel packages to Chicago, Illinois—a dynamic city known for its iconic skyline, deep-dish pizza, and world-class museums. These bundled vacation deals allow you to book both airfare and accommodations in one seamless transaction, often at a discounted rate.

The Ultimate Chicago Bucket List | Choose Chicago

With dozens of Michelin-starred restaurants and James Beard awards, Chicago’s fine dining restaurants draw in locals and visitors from all over. And while their food… · Looking for a vacation that’s more thrill than chill? In Chicago, you get to pick your own adventure. Discover the ultimate Chicago bucket list, featuring iconic attractions, unforgettable experiences, and must-try bites. Start planning your Chicago adventure today!There are so many ways you can do Chicago — and if you’re going for the first time, you’ll want to hit up all the classics and must-see spots.We’ve put together this definitive list of the essential Chicago things to do and see, from the city’s most iconic attractions to award-winning and under-the-radar restaurants.Eat classic Chicago pizza…and lots of it!

15 Astonishing Summer Road Trip Ideas from Chicago (Updated For 2025) – Windings to Unwind

From a quick 3-hour Chicago weekend getaway to 16 hours epic jaunt to the Rockies for seasoned road trip connoisseurs - use this Mega Chicago Road Trip thread to know more about 15 curated, off-beat Summer Road Trip ideas from Chicago - including nearest oceanfront beach from Chicago, dreamy ... From a quick 3-hour Chicago weekend getaway to 16 hours epic jaunt to the Rockies for seasoned road trip connoisseurs - use this Mega Chicago Road Trip thread to know more about 15 curated, off-beat Summer Road Trip ideas from Chicago - including nearest oceanfront beach from Chicago, dreamy Michigan coast towns, bridge walk under…From a quick 3-hour Chicago weekend getaway to 16 hours epic jaunt to the Rockies for seasoned road trip connoisseurs – use this Mega Chicago Road Trip thread to know more about 15 curated, o…From a quick 3-hour Chicago weekend getaway to 16 hours epic jaunt to the Rockies for seasoned road trip connoisseurs – use this Mega Chicago Road Trip thread to know more about 15 curated, off-beat Summer Road Trip ideas from Chicago – including nearest oceanfront beach from Chicago, dreamy Michigan coast towns, bridge walk under…Wide assortment of adventure activities for kids and adults, just 5 hours away. Best part is the simplified logistics since lodging, activities and even food is managed by Wildman itself. White-water Rafting – Wildman Resort is one of the nearest and well-managed white-water rafting spots from Chicago.

The 20 Most Romantic Getaways From Chicago for Couples

Chicagoans have been escaping to Lake Geneva since the late 19th century and the city is home to numerous resorts and vacation rentals. Get a sense of that history at Maxwell Mansion, which was built as a summer home in 1855 and boasts a cocktail bar with outdoor bocce ball courts and fireplaces. Skip town for luxurious resorts and relaxing spas.The most romantic getaways from Chicago boast charming bed and breakfasts, farm-to-table restaurants, spas and more.Chicago has plenty of romantic restaurants, but sometimes you want to wow your partner with more than just dinner. A weekend getaway from Chicago provides the opportunity to put aside the responsibilities and distractions of home and reconnect while making some memories.Driving time from Chicago: Four hours Spanning 300 miles of shoreline, the peninsula between Green Bay and Lake Michigan boasts numerous hiking trails and perfect spots to watch both the sunrise and sunset, plus spectacular stargazing at Newport State Park.

Chicago Things to Do, Events, Restaurants, Hotels & Vacation Planning

Chicago is celebrating its 8th year as the Best Big City in the U.S.! Explore iconic attractions, hidden gems, and travel guides. Plan the perfect Chicago trip! This bold new initiative calls on residents and visitors to share their unapologetic, authentic, and unfiltered stories about why they love Chicago.Together, let’s take back Chicago’s story and show the world what our city is really about.Chicago is a city with many sides, but they all come together to tell our story.This new initiative is about taking back our city’s story and showing the world the real Chicago.

Chicago Vacation Packages | Getaways by Southwest™

Find the best deals on vacation packages to Chicago when you book your next trip with Southwest Vacations.

Chicago Vacation Packages - American Airlines Vacations

External link. Go to American Airlines Vacations core website. Vacation packages from Washington, D.C. to ChicagoVacation packages from Dallas-Fort Worth to ChicagoExternal link. Go to American Airlines Vacations core website.

Chicago Vacation Packages 2025 | Delta Vacations

More than just another big city, Chicago’s Midwestern soul will make you feel right at home. Chicago Vacation Packages · More than just another big city, Chicago’s Midwestern soul will make you feel right at home. Whether it’s your first time visiting or a weekend getaway, there are lots of ways to experience America’s Second City.Getting to Chicago · Delta Vacations flight + hotel packages include round-trip airfare aboard Delta to O’Hare International Airport (ORD) or Midway Airport (MDW). To get into the city and to your hotel — car rentals, taxis and shared vans are available, as well as bus and train options.Make the most of your vacation by exploring the U.S. with a rental car from Alamo, Enterprise or National. See the sights, take the family out to dinner, and explore all this fabulous destination has to offer with the freedom of a rental car. Plus, the primary driver may earn up to 500 bonus miles per rental and an additional 200 bonus miles per rental day, through the SkyMiles® Program in the U.S.Your elevated vacation experience starts here.

Chicago Ultimate Getaway Roundtrip from New York City | Amtrak Vacations®

Depart from New York City on a rail journey to one of America’s most fascinating cities! Spend four fun-filled days in Chicago, the “Windy City”. Learn More! Discover all options for customizing your rail vacation!See a rail vacation package you like, but it would be even better with an extra day at the beginning or end of the journey? Or an extra day in between in a different destination?

Chicago+Boston 6-day, 5-night in-depth itinerary plan 2025: Explore Chicago+Boston's popular attractions (updated September)

Explore NatureCultural HistoryLeisurely VacationFamily-FriendlyOutdoor RecreationShoppingGourmet FoodHotelsDrivingWater RecreationPromotionInflight TipsGreen TravelTravel TipsHoliday CalendarCOVID-19 ... Explore the latest travel routes for your 6-day, 5-night tour of Chicago+Boston in 2025, ... Explore NatureCultural HistoryLeisurely VacationFamily-FriendlyOutdoor RecreationShoppingGourmet FoodHotelsDrivingWater RecreationPromotionInflight TipsGreen TravelTravel TipsHoliday CalendarCOVID-19 ... Explore the latest travel routes for your 6-day, 5-night tour of Chicago+Boston in 2025, featuring comprehensive itinerary planning, a travel checklist, and recommendations for transportation, accommodation, and attractions to ensure an enjoyable trip.Route 66 is affectionately called "Mother Road" by Americans. Route 66 runs diagonally from Chicago to Santa Monica, California. Route 66 total length: 2448 miles (about 3939 kilometers). Construction of Route 66 began on November 11, 1926, and was only announced as complete in 1938.It begins in Chicago, Illinois, and runs through Missouri, Kansas, Oklahoma, Texas, Arizona, and diagonally across the U.S. territory to Los Angeles, California (later extending to Santa Monica). ), spanning eight states, three time zones, and a total length of 2,450 miles, or about 3,943 kilometers.Millennium Park is a large urban park in Chicago. One side of the park is Chicago's more prosperous Michigan Avenue, and the other side is the scenic Lake Michigan. In the park, the imprint of post-modern architectural style can be seen everywhere, so some people regard this park as a concentration of post-modern architectural style.

Top experiences for solo travelers in Chicago | Choose Chicago

You’ve got to make Chicago your next solo travel destination! It’s so easy to find something you love from outdoorsy bike trails to award-winning museums… On the shores of Lake Michigan, you can sit on the sand or even swim at Oak Street Beach and enjoy the waves and stunning views of the downtown Chicago skyline. Grab lunch at the Navy Pier Food Experience Corridor and bring it over to the beach for a solo picnic.Chicago has so many museums to choose from, but one of the best for a solo traveler is the Museum of Science and Industry. With highly interactive exhibits and unique pieces like a full U-505 submarine, you could spend hours here on a solo trip. Wander through exhibits like the Science Storms tornado simulator or get tickets for a show at the Giant Dome Theater.It’s not really a solo trip to Chicago without deep dish pizza, right? Choose the tour option that best fits your schedule and mobility needs and sample some of the city’s best bites with a small group of other travelers.A walk through Millennium Park is one of the best solo travel activities in Chicago, because there’s so much to do and see. Take the iconic photo at Cloud Gate (better known as “The Bean”), then move on to the Crown Fountain and the Lurie Garden for a moment of peace amongst the native blooms.

31 Best Day Trips to Take From Chicago

Want to vacation close to home? Enjoy Midwest beer, food and nature on these easy and affordable day trips from Chicago. Lake Geneva has long been an accessible weekend destination for wealthy suburban Chicago families, but no matter your budget, a quick retreat to this idyllic vacation town is sure to be a blast. The town rests on Geneva Lake, an 8-square-mile body of water made for summertime fun.Sometimes, you just want—sometimes need—a little escape from the city. If a full-blown weekend getaway isn't in the cards but you're still yearning for a change in scenery, there are plenty of options for a day trip within a few hours’ drive of Chicago.Spend an afternoon soaking up the rays on beaches along Lake Michigan, go hiking near Chicago in one of Illinois' stunning state parks or sample a variety of beers and cheeses up north in Wisconsin. The attractions are endless, ranging from amusement parks and Japanese gardens to eye-opening museums and historic lighthouses.Escape the crowded Chicago lakefront and head for the sandy shores of the Mitten State, where the water’s warmer and clearer. Soak up some rays and then stroll down Whittaker Street to peruse cute shops and art galleries. Book a spa treatment at The Harbor Grand Hotel for some rest and relaxation; adventurers can rent a kayak or paddleboard from Third Coast Paddling and go exploring along the Galien River.

Chicago Vacation Packages 2025/2026 from $342 | Travelocity

Looking for exceptional deals on Chicago , IL trips and vacation packages? Save when you bundle your flight and hotel. Book your trip today! You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants. Michigan Avenue · A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.Navy Pier ... Get ready to be surprised — you can vacation in Chicago for as low as $342.At Travelocity, we save you money and hassle with our excellent vacation packages. With hotels, flights and tours all in one place, why wait any longer? ... Typically, 2 nights is what most tourists book for their Chicago trip.Chicago which includes a skyscraper and street scenes as well as a family · Willis Tower showing a high rise building, mist or fog and cbd ... St. Louis VacationsAbsolutely — combine your flight, car and hotel into a Chicago vacation package and you can save a tidy sum. With so much to see in Chicago, having your own wheels will make exploring a joy.