Sofitel
If you want to plant yourself smack in the middle of classic Chicago food, shopping, and sight-seeing (thus eliminating the need for car/parking stress), Sofitel is the spot for you. Located steps away from the Oak Street shops, and surrounded by more stellar Chicago eats than you can count, Sofitel can help you vacation in comfortable luxury. We've got our eye on the Romance Package, which includes champagne and chocolate, but that's just us. Sofitel Chicago Watertower, 20 East Chestnut Street (at State Street); 312-324-400.
Longman & Eagle Inn
If your style steers you toward a more secluded spot, away from the downtown hustle, you need a night or two at Longman & Eagle's Inn. The Inn is literally upstairs from Michelin Star-winning Longman & Eagle, which means a few things. First, you know exactly where you'll be dining on your staycation, and you know it will be complete heaven. Plus, you've got first dibs on a table for brunch, just hustle downstairs! Any place where we're just steps away from late-night cocktail cravings is ok by us. The inn has just six rooms, so plan in advance.
Longman & Eagle, 2657 North Kedzie Avenue (just North of Milwaukee Avenue); (773) 276-7110.
Yolk
It's not a vacation until you've enjoyed a leisurely brunch. We've got our eye on Yolk, the upbeat, feel-good way to enjoy your eggs in the morning. Yolk has three locations, and we're partial to the River North area. Check out their (adorable!) website in advance to give yourself a little something extra to look forward to. We literally cannot stop thinking about the Tuscan Fritatta. Yolk, 747 North Wells Street (at Chicago Avenue); 312-787-2277.
Atwood Cafe
For a classier, downtown brunch vibe (perhaps after a night of vacation-esque reveling) we recommend Atwood Cafe. This is where you'll find the grown-ups doing brunch. Relax, stay awhile, and tell us all about the Apple Cider Donuts. Please. Atwood Cafe, 1 West Washington Street (at State Street); 312-368-1900.
Play 18 Holes—in city limits!
Believe it or not, our city is home to six golf courses. Give your sporty side the attention it deserves and relax on the links. We must admit, it does sound pretty cool to golf with our fair city as the backdrop. Just don't keep score this time, you're on vacation. Visit the Chicago Park District for golf course locations.
Couple's Massage at The Peninsula
You knew we wouldn't send you packing without a massage. Make sure you and your honey are on the same relaxed page and get a massage for two. Go straight for the best and book your appointment at the Peninsula, a local fave. We wouldn't be surprised if you started reliving this part your staycation on a regular basis. The Peninsula, 108 East Superior Street (at Michigan Avenue); 312-573-6766.
The Fireworks Navy Pier
Starting this May, the Fireworks at Navy Pier return to Chi-town. Before you insert an eye-roll, stop and think. Isn't it time you mellowed for a moment and appreciated classic Chicago, without entertaining someone else? This show is just for you, and we must admit that the romance factor of sitting beneath a colorful sky is too good to pass up. Fireworks are on Wednesdays and Saturdays, check the schedule to be safe.
See a movie at Piper's Alley
You didn't recognize a single best picture nominee during the Oscars this year. It's time to go to the movies. We love Piper's Alley because we're likely to find foreign and indie films here that you might not find anywhere else. Located in the heart of Gold Coast fun, your out night will almost plan itself. Piper's Alley, 230 West North Avenue (at Weiland Street); 312-664-8844.
Book a Pet Sitter
While you're away, make sure everything stays copacetic at home. Your little furry friends will need looking after, and you'll want to minimize the stress of getting that accomplished. Rather than running back to the house twice a day, save yourself the headache (and gas money!) and hire a pro. We love Urban Out Sitters, because they offer cage-free dog boarding, and in-home cat care, so everyone is safe, cared-for, and happy.
Hire A Maid Service
With all that cash you saved by avoiding airfare, you can totally indulge in a spruce-up for your home. Hire Sparkle Queen, Chicago's favorite (and eco-friendly!) cleaning service to pay a visit to your pad while you're away. You'll come home to a fresh-n-clean house, making those staycation feelings linger just a little bit longer.