The 10 Cheapest City Pairs for a Multi-City Trip

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The best things in life come in pairs. 

Yeezys. Reese’s Peanut Butter Cups. Hobbs and Shaw. 

Amazing vacations can also come in pairs — specifically, pairs of cities. Imagine, for example: You’re traveling from the East Coast to Los Angeles. You’ve already criss-crossed the country, why not maximize your time out west and visit another nearby city while you’re out there? 

The same principle is true for just about any trip. It’s what we call a twofer — essentially, double the vacation (Twice the sites! Twice the fun!) for the price of one. 

And finding the cheapest city couplings is something we here at Wanderu are uniquely situated to do, with bus, train and flight tickets all in our inventory. After sifting through our database to pinpoint the 100 largest cities in the U.S. within 250 miles of each other, we then looked up the following:

  • the average price of flights arriving into City A,
  • the average price of flights departing from City B,
  • and the average price of transportation between the two cities. 

From there, we were able to determine the cheapest combinations and ranked them accordingly. Below, we’ve plotted them in a table — 10 city duos destined to make your trip doubly awesome.

Flight Into Bus/Train Between Flight Out Of TOTAL
Las Vegas to L.A. $105.42 $22.20 $149.06 equal $276.68
Portland to Seattle $121.13 $26.08 $133.24 equal $280.45
San Jose to Sacramento $131.49 $26.63 $136.32 equal $294.44
Orlando to Tampa $148.80 $13.51 $144.05 equal $306.36
Milwaukee to Chicago $166.96 $13.43 $137.33 equal $317.72
Cincinnati to Indianapolis $132.07 $14.05 $175.01 equal $321.13
San Diego to Long Beach $168.42 $23.91 $142.50 equal $334.83
San Antonio to Austin $154.59 $11.73 $172.02 equal $338.34
Buffalo to Cleveland $163.84 $34.60 $177.95 equal $376.39
Baltimore to DC $199.61 $14.35 $188.16 equal $402.12
  • Bus & train prices are based on the average cost of a one-way ticket (on either a bus or train, depending on what is available and/or cheapest) for the respective route available on Wanderu over a 30-day period.
  • Flight prices are based on the average cost of domestic, one-way tickets into and out of the respective airports over a 12-month period.

The Twin Cities may not have made the cut (they’re just too close to each other to be considered distinct destinations), but the rest of these twosomes are both twinning and winning when it comes to tandem trips. 

The list above is ranked by the cheapest total travel price, and is comprised of city pairs across the country. It’s important to note that the average listed plane ticket prices are for domestic, nonstop flights. And because these are just averages, there’s a good chance you score an even better deal. (After all, your own total cost will be dependent on where you’re flying in and out of, and how far in advance you book.)  

Even better, since we introduced flights in October 2019, you can book every leg of your journey — plane, bus and/or train — all on Wanderu, your one-stop shop for travel booking. 

Now, let’s take a closer look at each trip and why it’s worth your time. 

1. Las Vegas to Los Angeles

If L.A. is the City of Angels, then Las Vegas is the devil on your shoulder. In a single trip they balance each other perfectly, like sour and sweet. 

Vegas needs no introduction. From the craps tables to Christina Aguilera: The Xperience, there’s truly something for everyone in the desert. (Sleep is optional, but recommended.) 

Pair that with the town of tastemakers — Los Angeles, just a five- to six-hour bus ride away. Cheer on the Lakers from the nosebleeds, shop La Brea Avenue, hike to the Hollywood sign: There are a million ways to spend your time, not one of them wrong.

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2. Portland to Seattle

Photo of the Seattle skyline at night, with a view of the Space Needle.

These two Pacific Northwest gems pack the perfect 1-2 punch.

With a river splitting downtown in two, Portland is known for its bridges. (Cathedral Park, beneath the St. John’s Bridge, is a hidden gem.) It’s also known for its beer. Quirkier than its northern neighbor, you can take a goat yoga class or sign up for cuddle therapy. (Yes, that’s a thing.)

Once you’re cuddled out, board a bus for the three-and-a-half-hour ride up I-5 North to the Emerald City. Whereas Portland is gritty and hipster, Seattle is more polished and professional. At iconic Pike Place Market, you can watch fishmongers sling salmon and visit the Original Starbucks, opened in 1971. Then head to the University District for some solid vintage shopping.

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3. San Jose to Sacramento

Photo of the Leland Stanford Mansion in Sacramento.

We already shined a spotlight on L.A., but the northern half of the state offers its own awesome attractions. 

The gateway to Silicon Valley, you can learn about San Jose’s tech origins at The Tech Initiative. Or, opt for a walk through the Municipal Rose Garden — a fun (and fragrant) stroll.

Prepare to drink rosé all day after a four(ish) hour bus ride up to Sacramento. Cali’s capital city is rich with West Coast history, from the California State Railway Museum to the glammy Leland Stanford Mansion. Bonus: Sacramento also has the cheapest wine of any city in the U.S.

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4. Orlando to Tampa

Crowds walk down the Main Street in Orlando's Disney World.

This Florida tour pairs the pure joy of Orlando’s theme-park scene with the pristine beaches of Tampa Bay. 

Whether you’re a Disney fanatic, a Harry Potter head or a little of both (though we’ll call you a mudblood), Orlando is the premier destination in the country for epic amusement parks.

Couple that with a train ride 92 miles southwest to Tampa (at a little over two hours travel time). Nestled along the Gulf of Mexico, Tampa has some of the nation’s top beaches. (In fact, TripAdvisor named Tampa’s Clearwater Beach the best in the U.S. in both 2018 and 2019.) If you get sick of the sand (you won’t), the Big Cat Rescue offers a chance to see lions, leopards and ocelots in a respectful sanctuary setting.

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5. Milwaukee to Chicago

Photo of the Milwaukee, Wisconsin skyline, along the coast of Lake Michigan.

Chicago is ever the Second City, because Milwaukee is your first stop. 

Called the Cream City (because of all the dairy, duh), locals swear by Purple Door Ice Cream, with interesting flavors like Brandy Old-Fashioned, Campfire, and Fireball. Lick your cone en route to the Harley-Davidson Museum, where you don’t have to be a biker to appreciate these motorcycles’ majesty.

Two hours south (a 100-mile bus ride) is Chi-Town. Downtown is where you’ll find tourist hotspots like Navy Pier and the Willis Tower, but for food and drink we recommend venturing further afield. West Loop and Wicker Park are where it’s at, before you wrap the night at a late improvOlympic show. 

While we recommend flying out of Midway (it tends to be cheaper), if your city doesn’t have options out of the South Chicago airport, O’Hare isn’t a bad deal either — outbound tickets average $170.51. 

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6. Cincinnati to Indianapolis

Overhead view of Fountain Square in Cincinnati.

Tour two spots in the Midwest — the first rich with history, the second flashy and new. (Kinda like Carrie Fisher and Billie Lourd.) 

Cincinnati’s Over-the-Rhine neighborhood is a food and shopping district just north of downtown that has retained much of its stunning 18th-century architecture. Visit in March for Bockfest — think Oktoberfest, but with higher alcohol beer and a “Sausage Queen.” Cincy is, after all, the second cheapest drinking city in the entire U.S.

Then, two and a half hours west (by bus), glossy Indianapolis shines with an excellent art museum, tons of urban bike trails, and a very cool culinary scene. (Breakfast at Milktooth is comfort-food goals.)

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7. San Diego to Long Beach

Photo of a cruise ship at rest in the harbor of Long Beach, California.

Bask in sunny San Diego, where the tacos are top notch and you can find the best craft beer in the entire U.S. In terms of activities, you don’t have to be an animal person to respect the size and reputation of the San Diego Zoo, and La Jolla Cove’s warm water is ideal for snorkeling. 

From there, head 122 miles north (a two- to three-hour bus ride) to Long Beach. Located some 25 miles south of L.A., Long Beach is a destination unto itself — a chill haven from the bright lights of Hollywood and honking horns of Rodeo Drive. Known for being bike friendly, with charming paths that snake along Queensway Bay, Long Beach is a place to recharge. 

For those with “beach trip” on the brain, these two cities in combo earn a perfect 10/10.

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8. San Antonio to Austin

Photo of Barton Springs in Austin, Texas.

A pair of lonestar headliners, San Antonio and Austin pair classic Texas flare with hip dining and nightlife. 

The Riverwalk is what SA is known for (it’s nicknamed the River City), but nearby Southtown is better for food than the tourist traps along the water. For something truly unique, tour the Natural Bridge Caverns, full of Insta-worthy rock formations. 

Zip 80 miles northeast (a one-and-a-half-hour bus ride) to weird-tastic Austin. Called the “Live Music Capital of the World,” Austin is packed with venues for whatever genre you jam to (though we’re partial to Antone’s Nightclub). During the day, cool off with a dip in Barton Springs, a 3-acre natural limestone pool.

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9. Buffalo to Cleveland

Bounce between these two industrial hubs perched upon Lake Erie, each with their own vibrant personality. 

Buffalo is famous for, well, wings — and no one does chicken quite like Gabriel’s Gate. Down a plate after a visit to Frank Lloyd Wright’s enigmatic Martin House, or mix in an excursion to Niagara Falls, only 30 minutes away.

About a four-hour bus ride south along the lakeshore lies the Cleve. Without question, the main attraction here is the spectacular Rock & Roll Hall of Fame, and if that’s all you saw you’d still be satisfied. Even so, we suggest a stop at West Side Market for some quality food on your way to the Christmas Story House, where a leg lamp is still posed in the window.

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10. Baltimore to Washington, DC

Photo of the Smithsonian Castle in Washington, D.C.

From Baltimore to the Beltway, this trip explores two of the country’s most storied cities: The cram-packed capital and its harborside sidekick.

Charm City offers a walk back in time. Stroll the cobbled streets of Fell’s Point, a neighborhood that dates back to the 18th century, with coffee shops and art galleries aplenty. Then hit the Inner Harbor’s promenade, where you can sample the best seafood on the Eastern seaboard (crab cakes for days).

D.C., just an hour’s bus ride south, has it all — from the National Mall to loads of free museums. (We personally dig the Portrait Gallery, but here’s a guide to all the free attractions so you can choose for yourself.) Then there’s the White House, which you can wave at or flip off depending on your political proclivities. 

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City-to-City with Wanderu

So, what’s the hold up? 

Double up your trip with an additional stop by booking something from our list of the best destinations for a multi-city vacation. Changing up the scenery mid-vacation is the best possible use of your time (and dollars). Seriously, the duos above make up the cheapest combo deals since McDonald’s started asking, “Would you like fries with that?” 

The same trick works across the pond, too. Search cities in Europe to book multi-stop itineraries at the lowest possible prices. For instance, you could fly into London, take a coach to Paris, Amsterdam or Brussels, and fly out from there. 

Whatever your route, book it on Wanderu. Compare routes, schedules and prices for ground transport and flight options on Wanderu.com and the Wanderu app.

Methodology

We analyzed the following categories to determine the Best Destinations for a Multi-City Vacation:

  • Population
  • Distance between major cities
  • Average cost of flights into major cities
  • Average cost of flights out of major cities
  • Average cost of transportation between major cities.

Data sourcing:

  • For population, we pulled the 100 most populous cities in the U.S. from the 2019 World Population Review based on recent U.S. census estimates.
  • For distance between major cities, we used our internal Wanderu data to narrow the set to major cities within 250 miles of each other.
  • For the average cost of flights into major cities, we used our internal Wanderu data to calculate the average price of one-way, direct domestic flights arriving into each city’s biggest airport over the past 12 months. 
  • For the average cost of flights out of major cities, we used our internal Wanderu data to calculate the average price of one-way, direct domestic flights departing from each city’s biggest airport over the past 12 months. 
  • For the average cost of transportation between major cities, we used our internal Wanderu data to calculate the average price of bus and train tickets for a one-way route available on Wanderu over a 30-day period.

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About the author
Tyler Moss

Tyler Moss

Tyler Moss has danced on tables at Oktoberfest and petted alpacas in the Andes. He prefers to eat at restaurants where the menu is in a language he can’t understand, and likes bars where the lighting is dim and the drafts are cheap. His writing has been published by Condé Nast Traveler, The Atlantic, New York, Outside, Atlas Obscura, Playboy and other fine venues.
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