_{Expedia’s Best City Breaks – Please note: Many or all of the products featured here are from our partners, who compensate us. This may influence which products we write about and where and how the product appears on a page. However, this does not influence our evaluations. Our opinions are our own.}

Not every vacation needs to be a two-week escape. Sometimes, a long weekend is all you need to recharge, explore a new city, and indulge in local culture. Expedia makes it easier than ever to plan a quick yet unforgettable city break with flexible packages, exclusive hotel deals, and curated experiences.

Whether you’re craving art and architecture, buzzing food scenes, or a romantic rooftop view, the perfect urban getaway is just a few clicks away. Here’s a guide to Expedia’s top-rated city breaks for 2025—and how to make the most of a few days away.

1. New York City, USA

The ultimate city break for those who love energy, diversity, and 24/7 excitement. Expedia offers a wide range of hotel options in Manhattan, Brooklyn, and beyond. Book a Broadway show, enjoy fine dining, or stroll through Central Park—all within a few square miles.

• The Chatwal, a Luxury Collection Hotel
• Arlo Midtown
• The Ludlow Hotel

2. Paris, France

Perfect for romance and culture in equal measure. Expedia bundles often include flights, centrally located hotels, and museum passes. Even a short visit lets you sip espresso by the Seine, climb the Eiffel Tower, and explore world-class galleries.

• Hôtel Le Six
• Maison Albar Hotels Le Diamond
• Hôtel Alfred Sommier

3. Chicago, USA

Known for its iconic skyline, lakefront beauty, and deep-dish pizza, Chicago is ideal for a long weekend. Expedia’s deals often include top-rated hotels with views of Millennium Park or the Magnificent Mile.

• The Langham, Chicago
• Thompson Chicago
• 21c Museum Hotel Chicago

4. Barcelona, Spain

Colorful, artistic, and coastal, Barcelona offers the rare mix of beach and city life. Expedia’s vacation packages may include Gaudí architecture tours, tapas tastings, and boutique hotels in the Gothic Quarter.

• Hotel Arts Barcelona
• El Palace Barcelona
• H10 Casa Mimosa

5. Montreal, Canada

A favorite for North American travelers who want European charm without crossing the Atlantic. Expedia makes it easy to book French-inspired hotels, food tours, and bike rentals for Old Montreal.

• Hôtel Gault
• Hotel Nelligan
• Sofitel Montreal Golden Mile

6. Lisbon, Portugal

Affordable, walkable, and packed with history, Lisbon is quickly becoming a favorite long weekend destination. Expedia often offers 3- to 4-night deals with direct flights and boutique hotel stays in the Alfama or Bairro Alto districts.

• The Lumiares Hotel & Spa
• Memmo Alfama Hotel
• Santiago de Alfama

7. San Francisco, USA

A classic coastal city break. Ride cable cars, explore Fisherman’s Wharf, or walk across the Golden Gate Bridge. Expedia helps travelers pair direct flights with hotels in SoMa, Union Square, or Nob Hill.

• Hotel Nikko San Francisco
• The Fairmont San Francisco
• Hotel Zetta

Travel Tips: How to Maximize a Long Weekend City Break on Expedia

Book non-stop flights whenever possible
Cutting down on layovers means you’ll have more time to enjoy your destination. Expedia’s filters make it easy to select non-stop options.

Choose centrally located hotels
Urban getaways are all about access. Staying in or near the city center minimizes your time in transit and maximizes exploration. Use Expedia’s “City Center” or “Near Public Transit” filters when searching hotels.

Bundle your trip for savings
Use Expedia’s vacation packages to combine flight and hotel bookings. Not only does this often result in 15–25 percent savings, but it also simplifies your itinerary.

Travel light
Skip the checked luggage and opt for a carry-on. Most city hotels offer toiletries and amenities, and lighter bags make navigating subways and sidewalks much easier.

Plan one anchor activity per day
You don’t need to see everything in 72 hours. Focus on one main experience daily—a museum, a show, or a guided tour—and leave space for spontaneity.

Book early for weekend rates
Weekends are popular, especially in cities with frequent events. Booking early through Expedia ensures you lock in competitive pricing and better room availability.

Check out city passes and skip-the-line tickets
Expedia often includes or links to city pass options that bundle access to major attractions. These can save both time and money in destinations like Paris, New York, and Barcelona.

Final Word:

Whether you’re planning a solo escape, a romantic weekend, or a short adventure with friends, a city break is one of the most satisfying ways to hit reset. With Expedia’s extensive range of packages, flexible booking options, and curated experiences, your perfect long weekend is closer than you think.