Top 5 Major US Cities to Visit For a Weekend Getaway This Summer (2026)

Updated: December 31, 2025

Summer is the season that people move about.
I prefer to stay home in the summer and enjoy the weather while everyone else travels around. I try to make it my “off season.” That said, the travel still ends up happening. There’s always baseball to be seen in Chicago or great food to be had in NYC.

To me, summer travel is about weekends. A quick two-to-three-day trip to enjoy a great destination while their weather is also great. Without a ton of science behind it, I will reveal my list of the top 5 cities to visit in the U.S. for a weekend in the summer.

Remember, my blog is all about my experiences and providing you a foundation to kick off your own. There are far more places to stay, eat, and things to see than I lay out. Treat it as a starting point—and go from there.

5) Seattle, Washington

Public transportation from the airport: Easy | Around the city: Good

The Emerald City is one of my favorite weekend cities, but it shines in the summer and very early fall. Pike Place Market is always alive, and great food is just steps away. It’s a very walkable city, even with its crazy hills. The best part for me is the simple beauty of the city itself—but even more so the backdrop around it.

The people are also great, despite Seattle’s reputation for being standoffish. I’ve struck up conversations with many locals, even in touristy areas.

🏨 Where to Stay:

• Kimpton Hotel Monaco Seattle – A smaller IHG hotel in the heart of it all. Beautiful rooms, clean and quiet. My go-to in the city. It’s a 4-star hotel and can be pricey at times.
• Seattle Marriott Waterfront – A standard Marriott in a great location. Some reviews say it’s dated, but the views and people make up for any older furniture.
• MARQueen Anne Hotel – I have not stayed here. This hotel came with raving reviews from a local, and I almost stayed here but it didn’t work out. I researched it and the recommendation aligns, so I felt it worthy of the list.
• Hilton Garden Inn Seattle Airport – A bit from downtown, but one of the nicest Hilton Garden Inns I’ve stayed at. Great if you have points to burn or don’t mind being outside the city.

🍽️ Where to Eat:

• Alibi Room $$ (85 Pike St #410) – In the heart of Pike Place. The pizza is great, the baked brie is incredible, and the people are great. A+ location. It is on the fifth floor, near the famous gum wall.
• Purple Café and Wine Bar $$$ (1225 4th Ave) – Great food and wine with a very knowledgeable staff.
• Japonessa Sushi Cocina $$ (1400 1st Ave) – Excellent sushi and drinks at a reasonable price.

🚢 Extended Weekend Ideas:

• Ferry to Victoria, BC – 3 hours on the FRS Clipper. Victoria is beautiful and worth an overnight.
• Mount Rainier National Park – Rent a car and drive 90 minutes to some of the best scenery in the country.
• Ferries to nearby islands – I’ve been to Bremerton. Great food and vibe. You can even fit this into a normal weekend.

4) San Francisco, California

Public transportation from the airport: Easy | Around the city: Good

The City by the Bay always sparks controversy or interest when I list it in my top 5. Yes, it has areas with issues—like the Tenderloin—but it also has incredible beauty, food, and culture. The Mission District and Nob Hill are wonderful, and the Inner Sunset gives you a different vibe altogether. It’s a great city to explore with lots to see.

🏨 Where to Stay:

• W San Francisco – Pricier, but a great hotel in a good part of town. The bar and restaurant are excellent, and the rooms are large (for a city) and clean.
• Hilton San Francisco Financial District – I’ve stayed here several times. Large hotel, lots within walking distance, and often has great deals, sometimes under $200/night.
• Harbor Court Hotel – Beautiful hotel in the best part of town for exploring. My brother used this for his wedding guests, and it didn’t disappoint. About $160/night.

🍽️ Where to Eat:

• Ozumo $$$ (Steuart St) – Inside the Harbor Court Hotel. I went alone once and ended up staying for both happy hour and dinner. It’s still my most expensive solo meal—but worth it.
• Restaurants of Sausalito $\text{–}$$$$ – Just over the Golden Gate Bridge. So many great spots by the water. Take the ferry from the Ferry Building for the views alone.

🚗 Extended Weekend Ideas:

• Napa Valley – Just an hour north. Some of the most beautiful views in the world (not #1, but top 20).
• Half Moon Bay & Monterey – Beautiful coastal towns to the south.
• The East Bay – Berkeley and Walnut Creek offer a slower pace and great food, just 40 minutes away.

3) New York City, New York

Public transportation from the airport: Easy but long | Around the city: Amazing (best in the U.S.)

I could write about NYC for hours. It’s huge, and I’ve been countless times. If you just show up and do the tourist stuff, you’ll still have a great time, but it can feel overwhelming. A weekend here is perfect if you avoid staying in Times Square (unless that’s your thing). Every neighborhood has its own identity, and that’s what makes NYC, NYC.

🏨 Where to Stay:

• Hilton Garden Inn or Aloft Long Island City – These are top picks for me. LIC is in Queens, just one subway stop from Manhattan. Great value and LIC itself has a lot to offer.
• W New York Union Square – Union Square is a great area. You’re near a big farmers market and walking distance to Greenwich Village and Midtown. The hotel was just renovated.
• Millennium Hilton One UN Plaza – Great views and lower rates. It’s a short walk to most things, but I don’t mind that for the savings.

🍽️ Where to Eat:

• Gallaghers Steakhouse $$$$ (228 W 52nd St) – Classic old-school NYC steakhouse. Go for the steak, drink the wine. Worth every dollar.
• Turntable LP Bar & Karaoke $$ (34-36 W 32nd St, 5th Floor) – My favorite hidden gem in Koreatown. Amazing food, cocktails, and fun vibe.
• Ninos $$$ (1110 Hylan Blvd, Staten Island) – I’m not a huge Staten Island fan, but Ninos is worth the trip. Take the Staten Island Ferry (great views, free!) then a quick Uber to one of the best family-run spots in the city.

🚆 Extended Weekend Ideas:

• Just stay longer – NYC has way more than you can do in a weekend.
• Metro North to Upstate NY – Take the train from Grand Central to Mt. Kisco. Charming town, and don’t miss The Ambleside Pub!
• Amtrak for a short trip – Philly, Baltimore, DC, Connecticut, Boston, and more are all 1 to 4 hours away.

2) Boston, Massachusetts

Public transportation from the airport: Several options, some free, but it can take time—even though it’s so close | Public transportation around the city: Amazing (2nd best in the U.S. to NYC)

Beantown is an amazing city, but if this were just an overall list (not focused on summer), it wouldn’t rank as high. Winter in Boston is harsh, and while spring and fall are beautiful, they’re so short it’s hard to plan around them. July, August, and early September are Boston’s prime.

It’s such a walkable city, and when I say walkable, I mean if you’re ready to get some steps in, you can walk from one end to the other. From the Public Garden to Fenway Park to Quincy Market, there’s almost no better city to spend a summer weekend in.

🏨 Where to Stay:

• Encore Boston Harbor Casino – This hotel is one of the nicest on the East Coast. Yes, I mean that. The rooms are beautiful, and the service is five-star. It can be pricey, but worth it. Located in Everett, just minutes from downtown. Best part? They offer a free water shuttle (May to September) to downtown on a luxury boat.
• The Liberty, a Luxury Collection Hotel, Boston – It has a cool history as it is housed in a former 19th-century jail. Located in the heart of Beacon Hill, it offers easy access to the Charles River Esplanade, Boston Common, and downtown attractions.
• Canopy by Hilton Boston Downtown – Whether or not you stay here, ROSE Town Kitchen & Bar is one of the nicest hotel bars I’ve seen. This hotel may be in the best location of them all, along the Rose Kennedy Greenway, and just a short walk from almost everything (including my first food recommendation).
• Hotel Indigo Boston Garden – A solid Hotel Indigo, affordable and in a great location. The bar and restaurant attached are both very nice.

🍽️ Where to Eat:

• Riccardo’s Ristorante $$ (175 North St, Boston, MA 02113) – The best Italian I’ve had in the U.S. Family-run, five-star food, and five-star service in Boston’s North End. The price? Shockingly reasonable. I’ve been over 20 times. You can sit at the bar, share wine, apps, entrees, and dessert for under $75/person. Reservations are recommended on weekends, but not required.
• Legal Sea Foods $$$ (270 Northern Ave, Boston, MA 02210) – It’s now a “chain,” but it all started in Boston. I recommend the Seaport location for ocean views and the chance to watch planes take off from Logan across the water.
• Corner Pub $ (162 Lincoln St, Boston, MA 02111) – Exactly what it sounds like. This isn’t a full sit-down place. Order at the bar or by QR code. Known for creative egg rolls like steak & cheese or buffalo chicken.

🚂 Extended Weekend Ideas:

• Take the Amtrak Downeaster to Portland, Maine
• Take the ferry from downtown to Provincetown
• Rent a car and explore New Hampshire’s White Mountains

1) Chicago, Illinois

Public transportation from the airport: Very easy | Public transportation around the city: Great!

Number one is… drumroll please… well, you already saw it: Chicago.

There really is no better city to visit in the summer than Chicago. It’s like they figured out how to do everything right for the season. What do you want in a summer city?

• Nightlife on the water? ✔️
• Beach? ✔️
• Rooftop bars? ✔️
• Walkable neighborhoods? ✔️
• Great food with a great outdoor vibe? ✔️
• Great baseball? ✔️
• Friendly people? ✔️

Chicago hits every mark. It’s the perfect city for outdoor living. The Riverwalk is hands-down the best in the U.S. (Sorry, San Antonio).

I first visited Chicago in 2016, and my wife and I fell in love with everything it had to offer. We travel the world each year, but Chicago always makes it onto our mid-July calendar. It’s hard not to feel at home here.

🏨 Where to Stay:

• LondonHouse Chicago, Curio Collection by Hilton – An outstanding hotel. The views and location can’t be beat. The Riverwalk is just a two-minute walk. Everything else in the city is just steps away.
• The Westin Chicago River North – Same story as LondonHouse. The views may not be quite as spectacular, but the outdoor bar more than makes up for it.
• theWit Chicago, a Hilton Hotel – Another great option in the perfect location. Comfortable, well-priced, and stylish.

🍽️ Where to Eat:

• Lou Malnati’s Pizzeria (multiple locations) $$ – This is the place to try that legendary Chicago deep dish. There are other great spots, but Lou’s is my favorite. Try them all and let me know what you think.
• Harry Caray’s Italian Steakhouse $$$ (33 W Kinzie St) – Chicago is known for steakhouses, and this one is my go-to. A true Italian steakhouse with more than just steak (try the chicken parm!). The Kinzie St location is the original.
• Food and Drinks Along the Riverwalk $ to $$$ (306 to 370 W Wacker Dr) – Start at this address and walk east toward the lake. You’ll pass tons of great places. My favorite? Island Party Hut.
• Castaways Beach Club $$ (1603 N Jean Baptiste Pointe du Sable Lake Shore Dr) – Located right on the beach. Great spot for a drink or bite. I’ve only had drinks, but the vibe is fantastic.

🚂 Extended Weekend Ideas:

• Stay longer – Chicago can easily fill 4 to 5 days
• Take Amtrak to Milwaukee, Wisconsin (90 minutes). It’s on my top 5 list of small cities. Walk up and down Brady Street and enjoy “Brew City.”
• Rent a car and explore central and northern Wisconsin

Honorable Mentions

Narrowing this down to five was tough. Here are a few that almost made the cut:

• Minneapolis, Minnesota – Great anytime of year, narrowly lost to Seattle at #5
• Toronto, Ontario – If this included Canada, Toronto would be top 5
• Pittsburgh, Pennsylvania – A very underrated city, beautiful in the summer

Final Thought:
Every city has its own charm, and your preferences might be different—but if you’re ready to explore, these are my favorite weekend getaways.

Take a minute and let Google Flights help you find the best time to visit!

Do you have a summer city you love? Comment below!