7 Last-Minute Summer Getaways for Chicagoans

Get out now, before winter returns to crush your soul

last minute getaways
Escape to the Cayman Islands, anyone?
The Ritz-Carlton, Grand Cayman

News flash: with Labor Day fast approaching, fall is just around the corner, friends. And with fall comes winter, that ever-expanding period of misery where your radiator takes the place of your best friend and your booze of choice becomes your closest confidant.

But don’t despair just yet. We’ve still got a few more glorious weeks of summer to burn and as every Chicagoan knows, there’s no better way to stave off impending doom than with an epic end-of-summer vacation. Make the most of what’s left on one these seven stellar — and reasonably priced — escapes.

last minute getaways
(Caribe Hilton)

You’re going to: San Juan, Puerto Rico 

Round trip: $208 on Spirit

Briefly: Your last chance to get some sun before tundra season

Stay: The newly renovated Caribe Hilton is your new best friend. There are clean, comfy rooms with oceanfront views, a bunch of excellent bars and restaurants, several pools (ahem, including one with a swim-up bar), and a private beach. Plus it was the birthplace of the piña colada, so you know they do it right.

Must-dos: Laying out by the pool gorging yourself on piña coladas, obviously. Afterwards, check out to Old San Juan, where winding cobblestone streets dotted with shops, art galleries, museums, restaurants and a boatload of historic charm await. Don’t miss La Factoria, a world-class cocktail den with three different bars and frequent live music.

last minute getaways
(The Crawford Hotel)

You’re going to: Denver

Round trip: $104 on Frontier

Briefly: Bands, biking, baseball and beer, oh my.

Stay: If you opt for a city stay, book a room at The Crawford, a sleek, centrally located boutique hotel inside the restaurant- and bar-lined Union Station, Denver’s gorgeous Beaux-Arts train stop. For a backwoods escape, Breckenridge’s sweet and simple Breck Inn has you covered and then some (i.e., it’s got a hot tub).

Must-dos: Denver’s temperate climate and laid-back Western vibe are always a nice break from muggy, industrial Chi-town. Cheer on the Rockies while tasting the Rockies at Coors Field or take in a show at the scenic Red Rocks Amphitheater, arguably the country’s greatest outdoor concert venue. Then rent a car and head up the hill to Breckenridge, a picturesque ski town that transforms into mountain biking paradise come summer, complete with groomed trails, amazing views, and Breckenridge Brewery, a top notch brewpub ready to help you recover. Also, pot is legal, so there’s that.

last minute getaways
(Arai Aparthotel Barcelona)

You’re going to: Barcelona 

Round trip: $332 on Air Canada

Briefly: Only one of Europe’s sexiest and most culturally vibrant cities, no big deal

Stay: Budget shoppers, make a beeline to the Balmoral Hotel — stylish, super comfortable, and a stone’s throw away from pretty much everything you want to see, do, buy, and consume. Got a little extra cash to burn? Go with the four-star Arai Aparthotel Barcelona, an 18th-century palace turned art-strewn boutique offering uniquely outfitted rooms and a sweet rooftop pool in the heart of the Gothic Quarter.

Must-dos: In no particular order, you can’t leave without: marveling at Gaudi’s masterful La Sagrada Familia and Park Güell, people-watching along the tree-lined La Rambla promenade, stuffing yourself with jamón at the Mercado de La Boqueria, hitting up the Picasso Museum for some culture, embarking on a tapas and vermouth crawl around seaside Barceloneta, and clubbing till the wee hours in buzzy Port Olympic.

last minute getaways
Tabacon Thermal Resort & Spa

You’re going to: San Jose, Costa Rica

Round trip: $265 on Spirit

Briefly: Go hot-spring hopping in a sloth-filled rainforest

Stay: Rent a car or book a van from San Jose and make your way three hours northwest to Arenal Volcano National Park, home to a slew of breathtaking accommodations, many with private thermal pools. Keep it rugged at the Arenal Observatory Lodge & Spa, located deep in the heart of the park, or get swanky at Tabacon Thermal Resort & Spa with its high-end spa and massive network of cascading hot springs.

Must-dos: Between horseback riding, birding, hiking, kitesurfing on Lake Arenal, cacao and coffee plantation tours, guided nature walks along hanging forest bridges, ziplining, spelunking, sloth encounters, life-changing massages and sipping coconut cocktails at Tabacón’s hot spring swim-up bar, we’re pretty sure you’ll stay occupied. 

last minute getaways
(21c Museum Hotel)

You’re going to: Louisville 

Round trip: $199 on United or American

Briefly: Slow down and soak up the Southern comfort

Stay: The 21c Museum Hotel broke the mold when it opened its first location on Louisville’s Museum Row back in 2006, and the boutique brand continues to turn heads with its magical combination of design-forward guest rooms, a cutting-edge art museum, and multi-award-winning onsite restaurant. Come for the Ivan Navarro sculpture, stay for the bar’s 150-plus-bottle bourbon list.

Must-dos: Whiskey fans, start your engines. Wander downtown tasting rooms from the likes of Michter’s, Old Forester, Angel’s Envy, Peerless and Rabbit Hole or roam the pastoral grounds of Maker’s Mark, Four Roses, Castle & Key, Wild Turkey and more on a Mint Julep Experiences bus tour. For booze-free fun, pick up some fresh pine at the legendary Louisville Slugger Museum & Factory then get schooled on local history at the Frazier Museum or Muhammad Ali Center.

last minute getaways
(The Ritz-Carlton, Grand Cayman)

You’re going to: Grand Cayman 

Round trip: $340 on American or Delta

Briefly: Ball out on white sand beaches, and hug a stingray while you’re at it

Stay: If you’re looking for a taste of that resort life (hint: you are), you can’t go wrong with any of the luxe outposts scattered about Seven Mile Beach. The Ritz-Carlton, Grand Cayman is a classic and surprisingly wallet-friendly pick stocked with everything you need: spacious grounds, a stunning private beach and excellent onsite dining like Blue by Eric Ripert, a white-tablecloth seafood emporium helmed by the celebrity chef himself.

Must-dos: Between bouts of lounging on your beach chair and eating and drinking yourself silly, set sail for Cayman’s famous Stingray City, a shallow sandbar oasis where you can paddle around among fevers of friendly stingrays. Keep the nature theme going with a stop into the Cayman Turtle Centre, a major tourist attraction and conservation facility dedicated to majestic sea turtles, before joining the party at Rum Point, birthplace of the mudslide.

last minute getaways

You’re going to: Chicago

Round trip: $0 – $2.50 on CTA

Briefly: Culinary staycation with killer lake views

Stay: Plan the date night to end all date nights by treating your better half to the Exactly Like Nothing Else package at the Blackstone Hotel, a romantic four-star boutique stashed in a century-old Beaux-Arts building at the edge of Grant Park.

Must-dos: The promotion sets you up in the impossibly debonair three-room Smoke-Filled Suite before whisking you away for a private cooking lesson at the Michelin-starred Sepia or its sister restaurant Proxi followed by an elaborate five-course dinner. The next day, see your city with new eyes on a guided photo-op tour peppered with fascinating anecdotes detailing Chicago’s storied past. The price tag isn’t exactly cheap, but considering that you can literally walk (or scoot, your call) over to this game-changing getaway, it evens out in the end.

The InsideHook Newsletter.

News, advice and insights for the most interesting person in the room.