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Because they create frantic dashes from one gate to another, layovers are often panic inducing. Then there’s the stopover, a full day (or more!) between major flights, that allow for bonus exploration in cities as far flung as Hong Kong and Reykjavik—and have definitely become a recent trend among savvy travelers. But what about connections where you have anywhere from 4 to 8 hours between flights? This sweet middle spot allows for what we’re calling a “playover.” A playover happens when an airport is close enough to a downtown to make a day trip doable—without missing the flight. Not only is this a better way to pass time, but it’s a great opportunity to check big cities off your bucket list. So forget leafing through the latest gossip rags at Hudson News and instead add a playover itinerary in one of these great cities to your next vacation.

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Legal Harborside at the Envoy Hotel


Beantown is named for the baked dish, but Boston is also tiny like a bean and super easy to explore with little time! Logan Airport offers a quick and free bus to the Seaport District; or take an airport shuttle to the “T” which drops visitors downtown in 30 minutes.

If Seaport District bound, stroll the historic Boston Fish Pier where workers arrive at dawn to move fresh catches from boats to nearby eateries. Speaking of noshing on seafood, check out either Legal Harborside (those views!) or Outlook Kitchen at the Envoy Hotel. Afterward, stroll the 1.5-acre Rose Kennedy Greenway for selfies, then view a few masterworks at the waterfront Institute of Contemporary Art before circling back to Logan.

Seeking a more iconic Boston? Ride the “T” subway to downtown and exit at the Aquarium stop. First, check out the Old State House—site of the Boston Massacre. From here, walk one block to the Old South Meeting House—where the Boston Tea Party began. Next, walk 10-minutes to Neptune Oyster where you’ll wait in line (but thank us later) for killer lobsta’ rolls. You’re a stone’s throw to the Paul Revere House so check that out and while you’re there grab a cannoli from Mike’s Pastry before returning to Logan.

Cost: Free to Seaport District, $2.50 to return; $2.75 each way to/from downtown

Travel time: 18 mins to Seaport; 30 mins to downtown

Centennial Park


Take a bite out of the Big Peach! Aboard a downtown-bound MARTA train, a half-day playover in Atlanta is as easy and refreshing as a glass of sweet tea.

Ride either the Red or Gold line to the PeachTree Center stop. Upon arrival, walk 10 minutes east down Andrew Young International Boulevard to Centennial Olympic Park and check out the Fountain of Rings, a spectacular water display and direct antecedent to the Bellagio Fountains in Vegas. Where to go next? Both the Georgia Aquarium (think puffins, penguins and piranhas) and World of Coca Cola (think timelines, tasting rooms and TV ads) are a mere five-minute walk from the fountains and prime Atlanta attractions.

You’re not going to leave without filling your belly with Southern food, right? Jump in a taxi or ride share and zip down MLK Boulevard to beloved Busy Bee Cafe, an Atlanta fixture since the ’40s, and dream of fried chicken and buttermilk biscuits while waiting in the long queue. Afterward, zip back to downtown and take an Inside CNN Studio Tour (if there’s time) before returning to Hartsfield Airport via the Dome/GWCC/Philips Arena/CNN Center transit station.

Cost: $2.50 each way

Travel time: 20 mins to downtown

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Millennium Park


Stop whining about how much you hate O’Hare Airport and start marveling at world-famous art and architecture instead. Both Midway and O’Hare are connected to downtown via the city’s “El” rail system making a half-day playover in Chi-Town a cinch!

If coming from O’Hare, exit at the Washington stop and hit the ground running. Millennium Park is justly famous and includes numerous thrills within a span of few blocks. Snap a selfie in front of photogenic Cloud Gate (aka “the Bean”); stroll through magnificent Lurie Garden; then cross the Frank Gehry-designed BP Bridge to Maggie Daley Park for impressive Lakeshore views.

From here, stroll north along Columbus Ave and admire groovy Aqua Tower. At Wacker Drive, descend a flight of stairs and follow the Chicago Riverwalk past pretty flowerbeds, tourist boats and architectural icons like Marina City and the Wrigley Building. At State Street, walk south past the iconic Chicago Theatre and onward to Revival Food Hall. Grab some brisket at Smoque and a cookie for the road at Mindy’s Hot Chocolate before making the two-block walk to the Jackson stop for an airport return.

Cost: $2.50 each way

Travel time: 50 mins via O’Hare; 35 via Midway

Denver Union Station


Unless you arrive at Denver International Airport wearing cross-country skis, you probably won’t have time to hit the slopes. But did you know the MallRide will connect you to downtown’s revitalized Union Station and its many attractions in under 40 minutes for free?

A six-stop journey connects the airport to the city and brings visitors to Union Station, which underwent a dramatic transformation in 2014. The restaurants inside the station are not to be skipped and include the culinary stylings of several James Beard Award winners. Grab a seat at the bar at Mercantile Dining & Provision and enjoy farm-to-table fare like almond crusted halibut cheeks and duck confit; Ultreia is also helmed by a Beard winner. Afterward, try a boozy shake from Milkbox Ice Creamery.

Time to work it all off. Walk 10 minutes to Larimer Square, a historic district and site of Denver’s founding. Mercifully, the Square is largely free of chains and it’s worth perusing the boutiques and admiring the pretty lights strung up over the streets. Next, circle back toward Union Station via 15th Street, but this time stroll behind the building for a dose of greenery including Centennial Flower Gardens and Common Park. Both sit in close proximity to Elitch’s, an urban amusement park, but you’ve got another plane to catch so best return to Union Station for a ride back to the airport.

Cost: Free

Travel time: 40 mins to Union Station

The Park Las Vegas

Las Vegas

A city that sucks up money faster than a dust buster, Vegas is perfect for just a few hours and McCarran Airport’s close proximity to the Strip makes it easily doable via a budget-friendly WAX express bus.

In two stops, you’ll arrive at New York-New York. Walk north to the Park Las Vegas, Sin City’s charming desert playground, and check out 40-foot sculpture “Bliss Dance.” Afterward, do dinner at speakeasy-like Bavette’s Steakhouse inside the new Park MGM (save room for the cream pie). For a post-prandial libation, hit up Chandelier at the swank Cosmopolitan and order the off-menu “Flower Drink.”

Ditch the crowds in front of the Bellagio Fountains and instead see the show from Hyde Bellagio (there’s no cover before 10pm). Next, cross the street and press your luck at the LINQ Hotel, stroll the bustling LINQ Promenade and ride the High Roller for stellar Vegas views before taking the WAX bus back to McCarran.

Cost: $2 each way

Travel time: 15 mins to the Las Vegas Strip

Tagged: Cheap Tips, Chicago, City, Destinations, Flights, Las Vegas, Types of Travel

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