Chicago Vacations from $400

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Your Chicago getaway

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. From Millennium ParkOpens in a new window to the Art Institute of ChicagoOpens in a new window, design your perfect itinerary and make unforgettable memories with ease through Expedia.

The Latest Chicago vacation packages

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $609, price is now $400 per person
$400
per person
Dec 16 - Dec 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $1,482, price is now $470 per person
$470
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $830, price is now $507 per person
$507
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,358 reviews)
Staff was friendly and the room was clean

Reviewed on Nov 3, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was $639, price is now $403 per person
$403
per person
Jan 5 - Jan 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $720, price is now $474 per person
$474
per person
Jan 22 - Jan 25
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)
We thoroughly enjoyed our stay at the Riu Hotel. The location was fantastic. You could go shopping or walk to the lakefront in 5 minutes. The rooms were modern and immaculate. The breakfast was included in our reservation and was great. We were also able to enjoy the rooftop bar with a heater. We would definitely recommend staying here

Reviewed on Nov 4, 2026

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Where to stay in Chicago

Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Stay near popular Chicago attractions

An aerial view of a baseball stadium surrounded by urban buildings.
Photo by © City of Chicago
Open Photo by © City of Chicago

Wrigley Field

9.0/10 (11,704 reviews)
Step into baseball's living museum where ivy-covered walls and a hand-operated scoreboard create timeless charm. Experience the electrifying atmosphere of Cubs games in this century-old "Friendly Confines."
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What to do in Chicago

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$24
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

$40
per adult
92% of travellers recommend
Art Institute of Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Chicago

Chicago Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $126 total per night from Nov 22 to Nov 23
$126 total
Nov 22 - Nov 23
Total with taxes and fees
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $138 total per night from Nov 9 to Nov 10
$138 total
Nov 9 - Nov 10
Total with taxes and fees
The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$119 nightly
The price is $141 total per night from Nov 23 to Nov 24
$141 total
Nov 23 - Nov 24
Total with taxes and fees
River Hotel
See all 5,546 properties in Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best Chicago Vacation Packages

Family-friendly Chicago vacation packages

Chicago is a vibrant city with a plethora of family-friendly attractions and activities, making it an ideal destination for a memorable vacation for the whole gang. Book one of Expedia's kid-friendly vacation packages to ChicagoOpens in a new window and embark on an adventure everyone will cherish. Use Expedia's handy filters to narrow down your search by the number of bedrooms to find spacious accommodations like the Residence Inn by Marriott Chicago Downtown / River NorthOpens in a new window, which has rooms with kitchens for added convenience. You can also use the location filter to find downtown Chicago hotels close to all the attractions, like the Embassy Suites by Hilton Chicago Downtown River NorthOpens in a new window or the DoubleTree by Hilton Chicago – Magnificent Mile.Opens in a new window

Where to stay

Downtown Chicago: Ideal for first-time visitors, Downtown Chicago offers easy access to iconic attractions like Millennium Park, Navy Pier, and the Magnificent Mile shopping district. Visitors can choose from a variety of hotels ranging from luxurious upscale properties like The Langham, Chicago to more budget-friendly options, like the Hilton Garden Inn Chicago McCormick Place. 

The Loop: Located in the heart of downtown, The Loop is known for its skyscrapers, theaters, and cultural attractions like the Art Institute of Chicago and the Chicago Symphony Orchestra. Hotels near The Loop are a great choice for those interested in history, architecture, and the arts. 

River North: This trendy neighborhood is known for its vibrant nightlife, art galleries, and upscale dining scene. Visitors staying at hotels close to River North like The Royal Sonesta Chicago River North or 21c Museum Hotel Chicago can enjoy easy access to attractions like the Museum of Contemporary Art and the Chicago Riverwalk. 

Lincoln Park: Situated just north of downtown, Lincoln Park is known for its leafy streets, historic homes, and the sprawling Lincoln Park Zoo. Enjoy boutique shopping, charming cafes, and easy access to the lakefront when you stay here at an affordable option like the Hotel Lincoln, or really splash out for a luxurious trendy experience at Claridge House, which is close to the park. 

Top things to do

Iconic landmarks: Choose hotels near Millennium Park, like The Westin Chicago River North or the upscale Kinzie Hotel, where you can marvel at the famous Cloud Gate sculpture and enjoy interactive exhibits at the Crown Fountain. Take a leisurely stroll along the Lakefront Trail or hop on a sightseeing cruise on Lake Michigan for breathtaking views of the city skyline. Stay in hotels near Lincoln Park to visit the Lincoln Park Zoo, one of the oldest zoos in the United States, which offers free admission and is home to a diverse array of animals from around the world, sure to delight visitors of all ages. 

Museums and cultural attractions: Discover Chicago's rich cultural heritage at world-class museums like the Field Museum, home to Sue the T. rex, and the Museum of Science and Industry, where interactive exhibits ignite curiosity in visitors of all ages. Don't miss the Shedd Aquarium and Adler Planetarium for immersive learning experiences. Many museums and attractions offer special exhibits and programs designed specifically for families, providing engaging and educational opportunities for children to learn while having fun. 

Entertainment and shows: Catch a Broadway musical or comedy show at one of Chicago's renowned theaters like the Cadillac Palace Theatre or the Chicago Shakespeare Theater. Experience the magic of live performances at Navy Pier's iconic Crystal Gardens or the Chicago Children's Theatre. There's also the Chicago Children's Museum at Navy Pier, where hands-on exhibits and interactive play areas spark creativity and imagination in young visitors. 

Sporting experiences: Chicago boasts a rich sporting culture with attractions that cater to both fans and athletes alike. Key highlights include iconic venues like Wrigley Field and Soldier Field, home to the Chicago Cubs and Chicago Bears, respectively. Basketball enthusiasts can catch NBA games at the United Center, where the Chicago Bulls play. Additionally, the city offers opportunities for outdoor activities, such as golfing along Lake Michigan or sailing on the Chicago River. For those interested in sports history, the Chicago Sports Museum at Water Tower Place provides an immersive experience showcasing the city's athletic legacy. 

City vacation in Chicago

Experience the vibrant cultural scene of Chicago with Expedia's vacation packages, and immerse yourself in the city's rich heritage and artistic flair. Stay close to iconic landmarks at citizenM Chicago DowntownOpens in a new window or Hyatt Regency ChicagoOpens in a new window, and easily visit Millennium Park and the Art Institute of Chicago, where you can explore world-class exhibits and outdoor art installations. For a truly unique experience, opt for accommodations near the historic neighborhoods of Pilsen or Hyde Park, like The Hoxton ChicagoOpens in a new window with its rooftop swimming pool, or the Sophy Hyde ParkOpens in a new window, which boasts excellent guest reviews. 

How to find Chicago package deals

Browse Expedia's selection of Chicago vacation packagesOpens in a new window to find the perfect combination of flights, accommodations, car rental, and more. With Expedia, planning your Chicago getaway is simple and stress-free. Take advantage of special package deals and discounts on flights and hotels to Chicago, allowing you to maximize your savings while enjoying all that the city has to offer. Additionally, consider booking activities and attractions in advance to secure your spot and avoid long lines during your trip to Chicago.

Things to do in Chicago

Chicago offers a diverse range of activities perfect for families and outdoor enthusiasts alike. Explore vibrant shopping districts, catch a thrilling game at a local arena, or enjoy a captivating theater performance. Don’t miss iconic attractions and outdoor spaces, with plenty of free options available. Whether you're planning a day trip or seeking unique sporting experiences, Chicago's dynamic atmosphere ensures an unforgettable vacation.

Shopping

Woodfield Mall offers a diverse shopping experience with entertainment and family-friendly vibes. For a unique store visit, check out LEGOLAND® Discovery Center. Additionally, Chicago Place Mall features a blend of business and city vibes, making it an excellent spot for gifts and souvenirs.

Recreation

Experience the thrill of a Cubs game at Wrigley Field, soaking in the vibrant sports atmosphere. Enjoy a romantic evening at the historic Chicago Theatre, where culture and entertainment converge. For a lively night out, catch a concert at the Aragon Ballroom, enveloped in its captivating ambiance.

Adventure

Great Wolf Lodge Water Park offers thrilling water slides and a wave pool, making it perfect for family fun and adventure. Galloping Ghost is an exciting arcadeAdventureZone filled with classic games for all ages. For outdoor enthusiasts, Salt Creek Trail provides scenic hiking paths amidst nature's beauty.

Nightlife

Chicago's nightlife buzzes with excitement, featuring venues like Dave & Buster's for drinks and games, while Kingston Mines and Blues on Halstead offer vibrant nightlife with live music and romance. Experience the city's energy and charm as you explore these lively hotspots.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Chicago

Chicago is a vibrant city perfect for family and outdoor vacations, offering a variety of attractions such as urban parks, beaches, and modern universities. Visitors can explore cultural sites, enjoy family-friendly experiences, and discover the beauty of the Chicago River and Riverwalk. Whether you're looking to dive into the city's rich history or simply enjoy the urban landscape, Chicago has something for every traveler.

  • Navy Pier: Experience the vibrant atmosphere of Navy Pier, a bustling hub with stunning views of Lake Michigan. Enjoy entertainment, dining, and unique attractions like the Ferris wheel, all within a friendly and scenic environment.
  • Michigan Avenue: Known as the Magnificent Mile, Michigan Avenue is a bustling street lined with upscale shops, restaurants, and iconic architecture. Immerse yourself in the city's energy as you explore everything this urban thoroughfare has to offer.
  • Millennium Park: This urban oasis is perfect for families and outdoor enthusiasts. Enjoy beautiful gardens, art installations, and free events, all while soaking in the vibrant city vibes amidst lush greenery.

Best time to go to Chicago

The best time to visit Chicago is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.7°F (-3.5°C)Light RainMostly CloudySlightly LowSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudySlightly LowSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudyAverageAverage
April46.0°F (7.8°C)Light RainMostly SunnySlightly LowAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageAverage
June67.3°F (19.6°C)Light RainMostly SunnySlightly HighSlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly HighAverage
August73.0°F (22.8°C)Light RainMostly SunnySlightly HighAverage
September67.1°F (19.5°C)Light RainMostly SunnyAverageSlightly High
October54.9°F (12.7°C)Light RainMostly SunnyAverageSlightly High
November42.3°F (5.7°C)Light RainMostly SunnyAverageAverage
December33.1°F (0.6°C)Light RainMostly CloudyAverageSlightly Low

Tips to save on your trip to Chicago

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Chicago during the low season (December to February) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Chicago Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
2,720,500
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Chicago Riverwalk, John G. Shedd Aquarium and Art Institute of Chicago

Why visit Chicago

Indulge in culinary delights 
Savor the diverse flavors of Chicago's culinary landscape, from deep-dish pizza to gourmet hot dogs. Explore bustling food markets and indulge at Michelin-starred restaurants to discover why Chicago is a foodie's paradise. 

Experience thrilling sports action 
Catch a game at legendary stadiums like Wrigley Field and the United Center, home to the Chicago Cubs and Bulls. Feel the excitement of live sports and immerse yourself in Chicago's passionate sports culture. 

Discover architectural wonders 
Marvel at the iconic skyline as you admire architectural treasures like the Willis Tower and historic neighborhoods like the Magnificent Mile. From skyscrapers to historic landmarks, Chicago's architecture tells a fascinating story of innovation and design.  

Experience thrilling sports action 
Catch a game at legendary stadiums like Wrigley Field and the United Center, home to the Chicago Cubs and Bulls. Feel the excitement of live sports and immerse yourself in Chicago's passionate sports culture. 

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Frequently asked questions

What types of vacation packages are available in Chicago?
A Chicago vacation package can be built around several common travel styles:
  • Luxury: Nearly all hotels in Chicago fall into the luxury tier, offering premium amenities. For example, The Peninsula Chicago, a 5-star property rated 9.4 out of 10 by travelers, features family rooms, an indoor pool, and a spa, with travelers often highlighting its beautiful overall experience.
  • Family-friendly: Chicago is known for family-friendly attractions, and nearly a third of hotels offer family rooms, while most have kids clubs and playgrounds. The Langham, Chicago, a 5-star hotel rated 9.4 out of 10 by travelers, provides family rooms, an indoor pool, and a hot tub, and is praised for its beautifully appointed rooms.
  • Budget: A select few hotels cater to budget-conscious travelers, offering more affordable stays.
  • Pet-friendly: Many hotels in Chicago welcome pets, though policies and fees can vary.
  • Breakfast included: Most hotels in Chicago offer complimentary breakfast, adding value to your stay.
How much does a Chicago vacation package cost?
A Chicago vacation package typically costs around $700 per adult for a weekend trip. Lower-priced bookings start from around $400 per adult, while luxury options can reach up to $1,500.

*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
How do I find cheap Chicago vacation package deals?
The cheapest Chicago vacation package deals can be as low as around $370 per adult for weekend trips. Separately, January and February typically have the lowest average monthly prices, around $490 to $510 per adult, typically for a 3-day trip. Bundling flights and hotel together also typically saves money on a weekend trip — most Chicago vacation package deals include some savings versus booking separately, typically around $65 per adult. Longer, two-week trips can save even more, often around $155 per adult. Many hotels also include free breakfast, which can help stretch your budget.

Browse cheap vacation packages in Chicago on Expedia for current deals.

*Package prices shown are the average total cost per adult across Expedia bookings over the past year and may change depending on availability, dates, and demand.
What is the best time to go to Chicago?
The best time to go for a Chicago vacation package, in terms of demand and activity, is typically during the warmer months from June to September. July is often the peak month for demand, with many travelers choosing to visit during this period.

For those seeking a more budget-friendly Chicago vacation, prices are typically lower from January to February, and in December. While these months are quieter, they can offer a different experience of the city.
What's included in a Chicago vacation package?
A Chicago vacation package lets you combine round-trip flights, hotel stays, and rental cars. Nearly all hotels in Chicago offer airport shuttle service to and from major hubs like Chicago O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW). Most hotels also include free breakfast, which can be a convenient perk for city explorers.

Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
What's the best vacation package for Chicago?
For luxury Chicago vacation packages, consider a stay at The Peninsula Chicago. This 5-star hotel, rated 9.4 out of 10 by travelers and costing around $1,360/night, offers family rooms, an indoor pool, and a spa, with travelers often highlighting its beautiful overall experience and excellent rooms.

Families might enjoy a Chicago vacation package built around Radisson Blu Aqua Hotel Chicago. This 4.5-star property, rated 7.9 out of 10 and costing around $540/night, features family rooms and both indoor and outdoor pools, with guests often noting that their stay was beyond expectations and praising its fantastic location.

Couples looking for a romantic Chicago vacation package could opt for Thompson Chicago, by Hyatt. Rated 9 out of 10 by travelers and costing around $720/night, this 4.5-star hotel includes a bar/lounge and restaurant, and is praised for its great facilities and walkable location.

*Package availability and prices may change depending on dates and demand.
Is Chicago better suited for a beach vacation or a cultural trip?
Chicago is primarily an urban destination, known for its family-friendly attractions, city sights, and entertainment options. While it sits on Lake Michigan, the focus for a Chicago vacation is typically on its vibrant city life.

Travelers can immerse themselves in the city's rich cultural scene, exploring landmarks like Navy Pier, enjoying the public art and events at Millennium Park, or strolling along the Chicago Riverwalk. These attractions highlight the city's character as a hub for arts, architecture, and urban exploration.

Your Chicago vacation package can be customized to focus on these diverse urban and cultural experiences.
Is Chicago a good choice for a family vacation package?
Chicago is a strong choice for family vacation packages, with some bookings being family trips. Most hotels offer kids clubs, playgrounds, and babysitting services, and nearly a third provide family rooms. A select few even feature waterparks, adding extra fun for children.

For family-friendly accommodations, Embassy Suites by Hilton Chicago Downtown Magnificent Mile, a 4-star hotel rated 7.7 out of 10 by travelers, offers family rooms, free breakfast, and an indoor pool. Travelers frequently praise the great hospitality and free breakfast.

Families can enjoy attractions like Navy Pier, about 3 miles from central Chicago, which offers rides and entertainment, or explore Millennium Park, about 1 mile from central Chicago, known for its interactive art and green spaces.
Are luxury vacation packages in Chicago suitable for couples?
Luxury Chicago vacation packages are well-suited for couples, offering sophisticated stays with amenities designed for relaxation and enjoyment. Nearly all luxury hotels feature spas and hot tubs, and some provide multiple on-site dining options perfect for romantic evenings.

The Peninsula Chicago, a 5-star hotel rated 9.4 out of 10 by travelers, offers a bar/lounge, restaurant, and spa, with travelers highlighting the fantastic staff and beautiful overall experience. The Langham, Chicago, also a 5-star hotel rated 9.4 out of 10, includes a bar/lounge, hot tub, and indoor pool, with travelers often praising the beautifully appointed rooms and excellent location.

Another excellent option is Park Hyatt Chicago, a 5-star property rated 9.2 out of 10 by travelers, featuring a bar/lounge, hot tub, and indoor pool. Travelers frequently note the top-notch food and great rooms.

Explore luxury vacation packages in Chicago and romantic vacation packages in Chicago to find the perfect couples' retreat.
What luxury vacation packages are available in Chicago?
Chicago offers a wide array of luxury vacation packages, with nearly all hotels falling into the luxury tier. These packages often feature highly-rated 5-star properties:

Browse luxury vacation packages in Chicago on Expedia to compare options.
Which Chicago vacation packages include a pool?
Nearly all hotels in Chicago offer both indoor and outdoor pools, making it easy to find a Chicago vacation package with pool access.

The Robey, Chicago, a Member of Design Hotels, a 3.5-star property rated 9 out of 10, features an outdoor pool and spa, with travelers often praising its amazing rooms and wonderful breakfast.

Radisson Blu Aqua Hotel Chicago, a 4.5-star hotel rated 7.9 out of 10, provides both indoor and outdoor pools, along with family rooms, and guests frequently note that their stay exceeded expectations and highlight its fantastic location.

For a more budget-friendly option, Holiday Inn & Suites Chicago - Downtown by IHG, rated 7.7 out of 10, offers an outdoor pool and kitchenettes, with travelers appreciating its up-to-date rooms and great value.

Filter by pool type when comparing Chicago vacation packages to find the setup that works for your stay.
Do luxury vacation packages in Chicago include spa or wellness facilities?
Yes, luxury Chicago vacation packages often feature hotels with spa or wellness facilities, though specific treatments might cost extra. Nearly all luxury hotels in Chicago offer a spa and hot tubs. Top picks include The Peninsula Chicago, The Langham, Chicago, and Waldorf Astoria Chicago, all 5-star properties rated 9.4 out of 10 by travelers.

Browse luxury vacation packages in Chicago on Expedia to compare.
Are airport transfers included in Chicago vacation packages?
Nearly all hotels in Chicago offer airport shuttle services to help travelers get to and from major airports like Chicago O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW). While these services are a common amenity, they are typically provided by the hotel rather than being a direct inclusion of the vacation package itself. It's always a good idea to confirm shuttle specifics, such as shared versus private options and any associated fees, directly with your chosen hotel or package provider before booking.
What is the best time to book a Chicago vacation package?
Book your Chicago vacation package around 5 weeks before you travel. It gives you time to secure your preferred flights and hotel while rates are still competitive. Most travelers book between 2 and 9 weeks out.

From July to September are the busiest months for Chicago packages, so booking earlier is advisable if you're traveling during these times.
What are the top things to do in Chicago?
A Chicago vacation offers a wide array of urban attractions and experiences:

Consider taking a Chicago Architecture River Cruise, rated 4.8 out of 5 by over 25,800 travelers, for a unique perspective on the city's famous buildings. Browse and book things to do in Chicago on Expedia.
How many days do you need for a Chicago vacation?
Most Chicago vacation packages last around 3 days, with many travelers choosing weekend trips. This duration allows you to experience key attractions like the Chicago Riverwalk, Millennium Park, and Navy Pier.

Nearly a third of travelers opt for week-long trips, providing more time to explore the city's diverse neighborhoods and cultural offerings. A select few choose two-week trips for a more in-depth experience.
Is Chicago a good destination for a weekend vacation?
Chicago is an excellent choice for a weekend vacation package, as most travelers choose weekend trips to the city. A focused 2-3 day visit allows you to explore many of its iconic sights.

During a weekend, you can catch a show at the historic Chicago Theatre, shop along Michigan Avenue, and relax in Grant Park. While longer stays offer more in-depth exploration, a weekend in Chicago provides a memorable urban getaway.
Do you need to rent a car in Chicago, or is public transport enough?
For a Chicago vacation package, public transport is generally sufficient for navigating the city's central urban areas like Downtown Chicago, The Loop, and Magnificent Mile. These neighborhoods are often walkable, and the city's public transit system provides access to many attractions.

When arriving, nearly all hotels offer airport shuttle services to and from Chicago O'Hare Intl. (ORD) and Chicago Midway Intl. (MDW), making it easy to reach your accommodation without a rental car. While a car rental can offer flexibility for exploring areas further afield, it's not typically essential for a city-focused trip.
Are Chicago vacation package hotels conveniently located?
Chicago vacation package hotels are generally well-located, with many properties placing you within easy reach of the city's central attractions.

For example, The Langham, Chicago is about a 15-minute walk from central Chicago, offering convenient access to many downtown sights. Both Nobu Hotel Chicago and The Peninsula Chicago are situated about 1 mile from central Chicago, putting you close to the heart of the city's dining and entertainment.

When choosing your package, consider the proximity of your hotel to the specific neighborhoods and attractions you plan to visit.
Are there vacation package hotels in Chicago within walking distance of restaurants and shops?
Many Chicago vacation package hotels are conveniently located within walking distance of restaurants and shops, especially in the central urban areas.

For instance, The Langham, Chicago is about a 15-minute walk from central Chicago, placing you near various dining and retail options. Both Nobu Hotel Chicago and The Peninsula Chicago are about 1 mile from central Chicago, offering easy access to popular areas like Michigan Avenue (about a 10-minute walk) and the Chicago Riverwalk (about a 5-minute walk), which are known for their shops and eateries.

When booking your package, check the specific hotel's location to make sure it aligns with your preferred walking access to amenities.
Can I change or cancel my Chicago vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Chicago vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more with Member Prices on over 500,000 stays worldwide and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Chicago vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Chicago vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How can I save money on a Chicago vacation package?
When you bundle, you can save up to 30%*. To save money on a Chicago package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary
How do I find last-minute vacation packages to Chicago?
To find last-minute vacation packages to Chicago, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Chicago vacation packages?
Free cancellation on a Chicago vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Chicago vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Chicago getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Chicago vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.