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10 Ways To Celebrate Your Anniversary in Chicago

Written by  Cecilia Ehlenbach

Anniversaries: what should be a beautiful celebration too often becomes an anxiety-laden event as the planner struggles to come up with something special or original. Why ruin your special day worrying over the logistics? Concierge Preferred has a whole list of romantic Windy City ideas for you and your hunny.

Things To Do On Your Anniversary In Chicago

1) An evening on Lake Michigan

There’s something magical about nighttime in the big city and what better way to enjoy the brightly lit skyline than on an evening boat cruise? Odyssey Cruises at Navy Pier offer dinner cruises nightly with varying themes—Champagne Dinner Cruise, Fireworks Dinner Cruise, Sunset Dinner Cruise, Full Moon Cruise—all featuring cocktails and three wonderful courses. We like this cruise line best because they offer cruises all year-long so those with January anniversaries, never fear, you haven’t been forgotten.

2) Pampering for two

How about checking into a spa for a day or afternoon with your significant other? Allyu Spa in River North offers a variety of couples’ services from hot stone massages to infrared sauna therapy. They also offer a great Couple’s Mini Retreat package which includes a 60 minute massage, sauna time, side by side pedicures, and a complimentary glass of wine and restaurant gift certificate. And if you’d like a little separate time, there are also plenty of individual spa treatments.

3) Dinner and a show

Sometimes it’s alright to stick with a tried and true classic. Taking in a play at the legendary Steppenwolf Theatre Company, known for producing exciting and challenging work season after season, sets the bar for a very engaging evening, especially if you’re looking for something to talk about over dinner. And on the topic of dinner, we’d recommend Boka for contemporary American or Caminito Restaurant for Argentinean.

4) A garden escapade

Instead of picking up a bouquet of flowers for your lady (or man), why not take him or her to the flowers? The Chicago Botanic Garden has over 24 gardens perfect for strolling through with your loved one whether you stop by in spring or summer when the flowers are at their peak, in autumn as the leaves brilliantly change colors, or during the snow covered landscapes of winter (where you can also escape indoors to the garden greenhouses).

5) One night in paradise

If you’re really looking for some big city romance, why not check into one of downtown’s many glamorous hotels for a night? A hotel stay can add an extra bit of spice to the day (and night) for both out-of-towners and the Chicago couple in search of something a little out of the ordinary. And why not spring for something extra special by staying somewhere first rate like the historic Drake Hotel or the luxurious Sofitel Hotel?

6) ¡Muy delicioso!

While French food seems to ooze romance so can Mexican when your city plays host to a trio of world-class restaurants by chef Rick Bayless as Chicago does. And because each restaurant features a different price point, there are options for those looking to spend a lot or just a little. Bayless’ Topolobampo is the most elegant of the three with many specialty dishes such as a pan-roasted heritage hen and a Wagyu rib eye. Frontera Grill serves up fine dining dishes, like Bayless’ signature moles, but in a more casual dining environment. XOCO offers wonderful caldos (hearty soups) and tortas for those looking for a quick bite with their sweetheart.

7) A swinging speakeasy

How about a retro night out with jazz and great cocktails? The Green Mill Cocktail Lounge in Uptown, once a hangout of Al Capone, keeps the spirit of the '30s and '40s alive with its prohibition era décor and nightly performances (including its Thursday night live radio shows). And bring your dancing shoes—what better way to impress your lady or man than by twirling them around the dance floor to a sassy swing number.

8) Sharing a laugh

As the saying goes, the couple that laughs together, stays together. So why not check out a show at The Second City? For over 50 years, this Old Town comedy club has been spewing out the laughs and bringing the funny with their signature sketch comedy shows. The club also has a dinner/show package which includes preferred seating at the theater and a fixed price dinner at an area restaurant—this should take some of the pressure off.

9) An iconic ride

It’s a little cheesy, but what about a carriage ride through downtown? Starting at $40 for 30 minutes, carriages a great way to see the city in a completely new way. There are a handful of routes to choose from—down Michigan Ave. or State St., past the lake, through the Gold Coast, to Navy Pier—and the carriages run in all sorts of weather. Taking a ride on a chilly night? Stay warm together under an enormous lap blanket. Heading out in the rain? Check out one of the enclosed carriages. And if you’re feeling especially romantic, add on a dozen roses to give your lover.

10) And to top it off: dessert!

Everybody loves chocolate so why not give a little sugar to your sugar? Leonidas, the Belgian chocolatier, has a store right off of Michigan Ave. which should not be missed. Take a box of their truffles to-go or enjoy chocolates, gelato, or macaroons (or maybe all of the above) along with an espresso in-store or at the lovely outdoor café seating.

4 concierge prefers 10 Ways To Celebrate Your Anniversary in Chicago. See All

1 concierge Tips

Concierge Preferences

Eden Bernal prefers 10 Ways To Celebrate Your Anniversary in Chicago
September 1, 2012 at 14:31 PM

Concierge Tips

Mark Kraemer 2011-12-13 09:30
Great ideas! Don't forget to talk to your concierge as we can help plan the perfect night out... it's what we do!