Here in the Windy City, there is just so much to see and do that nailing down your options for a fun date idea or two can get a little bewildering! After all, we are the third largest city in the US, so we need to be able to entertain quite a few people! But just like Momma always said, the best things in life are free (or nearly so); Chicago certainly surpasses those expectations, in spite of our unpredictable weather! Here are a few topics to get your gears churning while you’re getting your PlanJam on!

Sight Seeing
We sure do have a lot to see around here! Besides our towering skyscrapers, our plethora of cultural communities and numerous historical landmarks, Chicago is also host to nine museums, two world-class conservatories, 16 historic lagoons, three major zoos and ten bird and wildlife gardens. What’s even better is many of these spots are in your own back yard! In Chicago, Man has intricately infused Nature together in perfect harmony. Aren’t you glad you live here?

Sports, Concerts and Performing Arts
Of course, let’s not forget about Da Entertainment! It’s no secret Chicago has plenty of great teams to root for and lots of great music to coincide with them, many of which are free or low cost to its residents! Of course, we also got our own version of Broadway, along with hundreds of movies being filmed here, which is why many major actors call Chicago home. So get dressed up (or down!), grab your sweetie and get out there!

Picnicking
Whether you are looking for a laid back afternoon under a secluded, shady tree or grilling up some mean burgers at the beach, Chicago has plenty to offer for everyone! With 33 fresh water beaches and 7,300 acres of public greenage, we sure do live up to our motto of being a City in a Garden! What’s more, so much of it can be appreciated in relative seclusion, allowing you and your date to really get to know each other on a more intimate level!

Getting Around Town
Leave the car behind and take public transit! Chicago has one of the best systems in the country, and just about every section of the city is connected by bus, train or passenger car, on top of all the cabs. You can also easily get just about anywhere on a bike around here, thanks to the glaciers flattening the landscape and for the City laying out designated biking paths on the streets as well as through the parks.

So, no matter where you two decide to go or what you want to do, there you are!

When people think of a romantic city, they’re probably thinking of Paris. Or Milan. Or even Casablanca. Well, all those fabulous locations have a little something more in common – they’re all sister cities to Chicago, and you don’t have to book a flight to ignite that flame! With so many superb restaurants located in tucked away neighborhoods that tap just about every culture, on top of all the unique beauty and brilliance, you certainly have nothing to worry about here! Take a look at some of these romantic date ideas!

Restaurants
Hungry? Then look no further than Chicago! Every appetite and budget is catered to here, from fine dining establishments overlooking the skyline to quaint, secluded corner bistros and everything in between, Chicago has something for whatever mood strikes you. What’s more, many of the best places in town don’t require reservations, so there is never an excuse not to go out and feed whatever craving you two may have!

Concerts and Performing Arts
There is simply no better way to polish off a great meal than to take in a show, be it at a jazzy night club or at a Broadway musical. Something in the middle, perhaps? Whatever you decide to do, you can be sure it’ll be a memorable evening! Of course, who could forget all the wonderful outdoor performances Chicago hosts in the summer, many of which are totally free!

Shopping
Looking for an exquisite piece of jewelry? How about a hard to find book of poetry? Flowers? Chocolates? Underground music? Whatever you need, Chicago has it, and shopping together to find such gems is a great way to make that love connection! Just be sure to bring the plastic!

Off the Beaten Path
One of the great things about Chicago is how there are so many beautiful parks, forest preserves, beaches, bike paths and trails to explore. Even in the dead of winter, the city is full of wildlife, if you just take a moment to see things the way Nature does.

Getting Around
While riding the Red Line train downtown may not seem to be the most romantic of things to do, riding a bike sure is, especially tandems! Any mode of transportation can be rented around here, even roller blades! Then of course, there are horse drawn carriages you can climb aboard, rickshaws, paddle boats and even yachts, many of which double as fine dining restaurants! Even if you two stick to your own two feet, any special place in Chicago is easily within your reach.

With the American palate in a constant state of change, seeking out a unique dining experience can be a real challenge when the kids are in town. You need to keep it on a budget, the food has to be quick, and you need to be able to score a parking spot. At the same time, you also need to be assured families are indeed welcome and the restaurant has something on the menu the kids will actually eat! Well I have some great news for you! I compiled a brief list of places to satisfy that special craving you got a hankering for that has booster seats at the ready! And since I’m also a mom, I made sure every restaurant listed is finger food friendly, too!

Ras Dashen: This Ethiopian restaurant has lots of mild and not too spicy items on the menu for them, and plenty of heat for you! The tables are spread apart enough so you don’t have to fold up the stroller, and the larger dining hall in the back is perfect for tots who can get rather vocal, without you feeling like you got dumped off into no man’s land.

El Cid: Show me a kid that doesn’t like tacos, and I’ll show you a kid that will happily eat here! The location on Milwaukee is better suited for families, since things are spread out a little bit better, and the parking at the CVS can’t be beat! Oh and mom – everything is cooked in vegetable oil, so this Mexican restaurant is even a little on the healthy side!

Andies Restaurant: Mediterranean never tasted so good, and these guys are sure to please! A lot of kids like falafel once they try it, and hummus and pita bread is an easy switch from chips and dip. And who knows, with all that Nom Nom Nomm-ing going on from you, they might just want to sample off your plate, too! (The Lakeview area has more ample seating and better parking!)

Manee Thai: Kids love noodles, so Thai is pretty much a gimme! What sets this place apart from other restaurants in the city is its location when it comes to being on the kid friendly side, since it’s housed in what used to be a family pancake house…so you know there’s plenty of space! That, and the parking in the area is pretty reasonable! Also, if you tell these guys to go easy on the spice and oil, they actually accommodate!

Gulliver’s: Give that pizza-hustling rodent the boot, because this place is not only makes a great pie, but it has a million other items on the menu, perfect for even the pickiest eater! There’s ample, free parking, plenty of seating, and lots of stuff to look at! Be sure to stop by Indian Boundary afterwards!

Unless you've been living under a rock for the past couple of months, you're well aware Illinois is now a smoke-free state. However, there are still plenty of places you can go where you are more than welcome to light up. Just keep in mind, they probably won't be selling food or alcohol, as 80% of their business needs to be coming from tobacco. Even so, here's a quick list of places to check out:

House of Hookah: Right on the corner of Belmont and Broadway, this hookah lounge offers 80 flavors of tobacco, along with specialty cigarettes for the world traveler in you. Oh and yes, while hanging out and chillin' with your friends, be sure to order up an espresso or tea! Or, go ahead and bring something in with you, because they're also BYOB!

Guess Hookah: Another place to hook up with a hookah and BYOB, this time in the Wicker Park area! This place is also a full scale retail shop in all that is sweet tobacco, just in case you want to revel in the ambiance in the comfort of your own home. The lounge also offers free Wi-Fi as well as plenty of games to while away the hours.

Sigara Lounge: This place is also in the Wicker Park neighborhood, but the difference here is, besides the tobacco, the coffee and tea, this place has beautiful belly dancers on Thursday through Saturday nights after 10:30! Not only is this place is the first of its kind here, but it's also the best: you can reserve a private booth, or lay back on the big throw pillows scattered in classic Persian ambiance!

Iwan Ries: Unless it's Cuban, you can get it at this downtown location, because these guys really do have everything! They're the oldest tobacconists in the entire country in fact! Their website really doesn't do this shop justice; you really need to see it for yourself! If you want a lunchtime break from the ordinary, come on in, do a little splurging and feel free to light it up right there and then... whatever "it" may be!

Capitol Cigar Store: Located on the corner of 63rd and Pulaski, this place is really hard to miss. The shop itself is nothing special, but trust me - you might want to bring the camera, because old White Owl will be sure to greet you! And ladies, that giant Indian (errr.. Native American!) likes it when you scope out what's under his loin cloth! (Your best viewing angle is from looking northeast from the front of the flower shop across 63rd!).

Find additional Hookah Bars & Lounges

Whether you met online, through a personals ad or got set up through a mutual acquaintance, a blind date is still a blind date. In these situations, it’s always best to meet in some open, public place and depart from there as well. It is also a good idea to select a location you like but don’t frequent and is not near your home. You never know if things will work out or not, and well… you might not want to take a chance on bumping into this person again. And don’t forget, before you leave, be sure to let someone know where you’re going. It also might not be such a bad idea to have that someone call you at a specified time, just in case you feel the need to pack it in early.

With that in mind, I have a few restaurant ideas for places that are slightly outside the regular stomping grounds and offer just the right amount of privacy, they’re light hearted and fun and, since you might be splitting the check, are not too pricey.

The Sphinx Café: I’ve yet to meet a person who doesn’t like falafel or kabobs, and for vegetarians and meat eaters alike, Mediterranean food is always a great choice! This place is an especially good choice, because belly dancing is just plain fun! And, if the night seems to be going well, feel free to stick around for when the place transforms into a night club!

Tandoor Fine Indian Cuisine: If Indian food is on your mind but you want to take it up a notch, as well as guarantee finding a parking spot, be sure to hit this place up! The food is terrific, the $10 buffet on Friday and Saturday nights is really good, and the overall décor is quaint yet has a touch of class. Be sure to grab a mango lassi!

Addis Abeba: Ethiopian food at its most delicious and fun! It’s a great place to experiment something new while getting a sampling of something familiar at the same time. And communal, sans silverware eating is sure to strike up a conversation or two!

Al’s Char-House: If you like it big and beefy and ain’t shy about asking for a takeout box, then this is the place to go! And, there’s always the bonus of getting a great steak without breaking the bank!

Horan’s Snug: When Irish comfort food and casual dining is what you’re craving but you want to steer clear of the commercial and tacky, then be sure to give this place a try. And if you both also happen to be Karaoke lovers, then you’ll find yourselves in absolute heaven on Saturday night!

It’s no secret Chicago is home to a huge Irish population, whether residents are fifth generation descendants or new to the country, right down to our own mayor. So, it’s only fitting we host one of the most popular St. Patrick’s Day parades anywhere in the world, along with a second one specifically geared towards those who live on da South Side! On top of that, we have a plethora of Irish pubs and restaurants to choose from and even a highly regarded Heritage Center! So even if you don’t have an ounce of green blood in your system, there’s no reason to not go a little green and take part in one of the city’s largest celebrations!

9th Annual Chicago Irish Film Festival - February 29th – March 5th: Kick off the festivities by checking out some great films new and old down in Beverly! Whatever your taste in cinema, there’s bound to be something you’ll enjoy!

South Side Irish Parade - March 9th: This is how real people party, as the South Siders know they got it going on! Since many Chicago Irish are Catholic, it’s being held a week earlier than usual so the parade doesn’t clash with Palm Sunday. And hey, this way, you Heathens get over a week to party!

St. Patrick’s Day Parade - March 15th: They dye the Chicago River green around 10:45 and kick off the parade at noon. (Don’t worry – the dye is non-toxic!)

The Abbey Pub: Anyone will tell you, if you’re going to pull an Irish pub crawl, this place is a must have on da list! On the 17th, they have a huge party in store for you! St Patrick's Day Bash featuring Sand Carvers, Larry Nugent, Dave Dunne, Danny Bur- , Irish Dancers, Bag Pipers & more! Chicago's best St Patrick's Day Bash for over 25 years. Great music, dance and Irish fun. Traditional Irish food will be served. $10.00

Horan’s Snug: This charming little pub just outside the western city boundary serves up great food and karaoke on Saturday nights! Good brew selection as well!

Irish American Heritage Center: If you want a pint of the dark stuff and you want true Gaelic to go with it, then check this place out! They start partying on the 14th and head straight into Paddy’s Day itself! The 5th Province Pub’s inside the building and is open on the weekends; its authentic theme will really make you feel right at home!

Just because you didn’t get paid this week, don’t think you can’t afford to take someone out on a date. You may have to venture outside the confines of the city, but it’s definitely possible. Just hop on the blue line and take it to the very last stop: Forest Park. It’s here that you can find a few destinations that are not only fabulously romantic, they’re cheap, too.

The other day I met up with my date and we headed over to Todd and Holland Tea Merchants, a one-of-a-kind store located in Forest Park’s famed Madison Street area. I’d been in there once before, and the aroma walking in was enough for me to fall in love. Every kind of tea imaginable can be found here, as well as lesser known flavors that will have you longing for more. Right away, the store’s owner approached and offered us a tea sample. Poured into a small glass, this “Waikiki Beach” Japanese green tea was a unique take on an old favorite. Even without adding sugar, the tea had a sweet taste and an even sweeter aroma, thanks to a bit of pineapple. This lightly flavored delight really did conjure up images of breakfast with fresh fruit on a far-off Hawaiian beach.

My date and I slipped into a calming, tea-induced trance. The owner invited us to open small sample jars of tea and smell them, giving us a better idea of the flavors behind the clever names. Quietly, we perused the spotless, carefully arranged shelves full of high-end merchandise and both wished we had brought our credit cards. But the experience that the store provides (which is free) left us both feeling relaxed and comfortable, and ready for a good meal.

Across the street and down a little ways was our next destination: a charming, lesser-known pub-style restaurant called Skrine Chops. I’d passed this place before and took a look at their menu. Shockingly, this place features a pork chop dinner for $8.00! That in itself caught my eye, and on this night, I was determined to find out what it was all about.

Stepping in, it’s hard to tell if the restaurant’s name fits the atmosphere. With tarnished wood tables, stuffed remnants of hunted deer and other animals, and a miniature train set that runs the entire length of the restaurant, it definitely shouts “rustic cabin,” not-so-much “chophouse.” Right away a waiter came by and gave us menus—consisting of only a page—and in only a few minutes we had chosen from this modest list.

My date and I sipped frothy beers in big mugs and watched families and couples wander in. The crowd was boisterous and cheery, and we didn’t feel we had to speak softly. Minutes later, two hot plates arrived: mine with a sizzling pork chop and a huge helping of mashed potatoes and my date’s oversized grilled chicken sandwich dripping with barbecue sauce. This sandwich has a twist: the mashed potatoes are spread on top of the meat! It seems strange, but it tastes great.

My chop was tender and juicy and everything you’d want from an indulgent chunk of meat. The mashed potatoes were creamy, hot and irresistible. Tangy barbecue sauce finished off the combination perfectly, and before I knew it, I was full.

When the bill came, I wasn’t worried. Even with both of our meals and both of our drinks, the tab was only $25! And I honestly felt that my meal alone would have cost $25 in any other establishment. In no hurry, my date and I sipped the last of our beers and took advantage of the cozy atmosphere.

It’s nice to have money, but don’t let a lack of it hold you back. There’s lots to do in both the suburbs and the city that are fun and romantic and won’t leave you broke. Check out Skrine Chops next time you’re hurting for cash.

Ladies, it’s time to go out for a night on the town. You’re gonna meet up with the girls and hopefully, later on, meet up with some guys. So you throw on your black stiletto boots, tight jeans, strappy low-cut shirt and accessorize with sparkly, dangly jewelry. Right?

Wrong. It’s time to spice things up. You want to stand apart when you go to the bar, am I right? My advice is: head to store B in Wicker Park. This upscale antique/thrift shop is full to the brim with classy accessories and rare clothing finds that will have you looking like an old-time movie star at a glamorous premiere.

I stopped in there a couple of weeks ago and the glimmer of style from an era past caught my eye with every unique handbag, cute hat and sophisticated fur coat. This is where you go when you want to liven up your wardrobe in a way that is completely new as well as old.

Beautifully decorated, this place gives me a vibe that I don’t usually get in antique stores. No stinky, dusty smell, no junk, nothing that made me cringe. Just upscale, good quality clothing in a soothing, relaxed environment. The exposed brick, pendant lighting and elegant chandelier certainly bring a modern feeling to the space.

Trying on a couple of hats, I thought back to a girls night out I had a few years back, where I loaned out some of my vintage hats to some friends before we ventured out and painted the town red. Sporting our unique style, we got plenty of interesting looks and lots of compliments. Store B has a great collection of hats, so grab your girls and try some on.

You’ll also find plenty of gift items here, like unique glasswares and captivating knick-knacks. Personally, I can’t keep my hands off the adorable handbags, some in shiny patent leather and some with intricate beadwork. You’ll only find the best of the best here, but expect to pay a hefty price for it. A vintage handbag in good condition will set you back between $50 and $100 dollars.

Ever thought of wearing a vintage party dress to a dinner party? Check out their dress racks and see if you can find something that you can pair with an old handbag or a awesomely gaudy necklace. Since a lot of the newer styles are throwbacks to the fashions of past decades, you won’t look outdated at all, just vintage chic.

When you’re shopping with the girls in Wicker Park, make sure to stop by Store B. It may make you change your mind about antiques.

As too many Wicker Park restaurants rise out of my price range, and Starbucks replaces Filter, the Earwax Cafe remains refreshingly the same. Don’t be disgusted by the name, which came from the record store in the same location on Milwaukee Avenue, near the North/Milwaukee/Division intersection in the heart of Wicker Park. The café is now a delicious breakfast, lunch, dinner and coffee spot. The Earwax Café makes a perfect place to relax with friends before a show at the Subterranean or after hunting for second-hand treasure at Myopic Books or Reckless Records.

Groups of friends can sit in one of the high-backed gold and red booths by the old circus posters of Ostrich Boy and the knife thrower and the golden horned dragon head on the wall. You can talk for hours over the bottomless coffee ($3.75) and eat breakfast at any time of day. Vegetarian or vegan friends can dine well on the meatless burgers made from soy, or black beans, tempeh (soy, barley and spices) and even a seitan chorizo burrito. I was impressed by the Reuben with seitan (wheat gluten) seasoned exactly like corned beef. I would recommend the chocolate soy shake with ribbons of chocolate syrup to anyone. Carnivores can go straight for the pulled pork sandwich ($7.50) or Jamaican Jerk chicken ($8.95) with mashed sweet potatoes and rice. Crunchy, gingery sesame coleslaw and seasoned thin French fries make excellent sides and the vegan carrot cake lets you claim that your dessert is socially responsible. Get all your daily servings of produce at once in the Garbage Salad ($8.95) with romaine, spinach, carrot, bell peppers, mandarin oranges, sunflower seeds, dried cranberries and honey mustard dressing.

There’s no wine or beer here, but a good selection of espresso coffee drinks and loose leaf teas like oo long, sassafras and medicinal teas to fight off a cold. The Blue Velvet berry smoothie and Peanut Butter Chocolate smoothie are fun and filling. If your friends need a good meal before or after hitting the nearby bars, Earwax Café is ready for you.

Be warned, Earwax Café is cash only. The flyers for local art and music shows covering the wall and the litany of graffiti in the bathroom keep it real. This is the type of humble punk art place that made Wicker Park cool to begin with. Look for videos to rent and independent magazines in the back and downstairs.

There’s nothing like old world charm hidden away in a modern metropolis. I went out for a night on the town a few weeks back, and I found a little place that warmed me from head to toe—with both the hot tea and the inviting atmosphere.

It couldn’t have been a more romantic night. It started out with Mozart’s Mass in C Minor at a performance by the Chicago Symphony Orchestra. Up in the dizzying gallery, I could see the tops of all the musicians’ heads and the glimmer of the brass instruments. Surprisingly, there were tons of young couples there, dressed their best, sipping cocktails at intermission.

All told, it was a great show, and the perfect place to go on a date. But the best came next, when we skipped over to Russian Tea Time, a nearby after-concert hangout that drew us in from the cold with its cozy charm. Walking in, the place is decked out in lavish burgundy fabric and overly ornate chandeliers. Dark wood accents provided a nice complement to the neat, white tablecloths on the cramped tables. Truly, I felt like I was back in “the old country” (if I could claim a country other than this one).

Right after nabbing a seat a friendly waiter came over. “Russian tea?” And that’s when the evening really started. The waiter brought out a tea cup and saucer, along with sugar cubes and lemon, and then filled the cup to the brim. It wasn’t until I had a cup of that steaming, robust black tea that I knew that my night out was going to last until the early hours of the morning. Russian Tea Time describes their “Russian Caravan” tea by saying that the “unique aroma and taste is reminiscent of the campfires of traders as they made the camel-ridden long journey over the Silk Road.”

The tea really does take you to another place and time. Every time I would put my cup down after downing a huge gulp, the waiter would return and fill it back up with more hot, black liquid. All in all, I probably had four or five cups, and each sip was as hot as the last.

The menu there was amazing. Not only do they serve every kind of liquor imaginable, they boast a large wine selection, a sizable martini list, and of course, beer. On this particular night, though, I was sticking with the tea. If I’d had the chance to really peruse the menu first, I might have gone for their “Full Tea Service” deal: for $22.95 per person, you get a pot of tea, scones, “savories” (appetizers) and sweets.

Instead we ordered borscht and the pumpkin vereniky, which was served with a dark onion bread. I dropped a dollop of sour cream into the borscht, a soup made of beets and cabbage and spiced to perfection. The pumpkin vereniky—small, delicate dumplings—was a refreshing surprise. We spread the butter thick on the soft, dark bread, and after even more tea, realized we were full. And once our feast was over, we found ourselves conveniently nestled in the most romantic environment, full of deep colors, soothing music, and the sounds of gentle whispers as couples enjoyed their desserts from a decadent menu of blintzes, tortes, strudels and ice cream. We held hands on the table and I glanced down and caught a glimpse of one of the tea quotes printed on the menu:

“As long as it’s hot and wet and goes down the right way, that’s all that matters.”
–Duchess of York

Around midnight we left Tea Time and caught a cab over to Greektown. We were ready to paint the town red, and we ended up at a little neighborhood bar called “Spectrum Bar and Grill.” On this particular night, there was a live blues band, being enjoyed by an older crowd. We headed for the high tables and chairs in the back by the darts, and cuddled and talked until the band started to play. Pendant lighting created eerie shadows on people’s faces, and here and there was a creepy guy lurking.

But later, almost as if by clockwork, the crowd changed. Younger couples and groups poured in and immediately started with lively discussions, changing the atmosphere completely. By then, me and my date had downed a few drinks and were ready to come out of hiding. As the night went on, the place got livelier, until our eyelids were droopy and our tab was high and we decided to call it a night. But not before exchanging hugs and kisses to end one of the most romantic dates I’ve ever been on.

Take it from me; start with tea and see where the night goes.