North Branch Bicycle Trail
If you and your date are into bike riding, then this is probably the trail you two are going to want to tackle! It’s 17 miles start to finish, but so easy breezy that you won’t even feel it, even if you aren’t in the best of shape. And hey – the price can’t be beat (it’s all FREE!) And, it’s very secluded yet safe trails allow plenty of PDA and getting to know you time, too!
Make an entire day of it, preferably on a week day when the temperature is just right, from dawn up to dusk. Plan ahead by packing two packs of everything you’ll need for your journey: plenty of water, energy bars, non perishable lunch items, sun block, and a large blanket to lounge on. (Remember to drop some ice in your water bottles, too!) No glass is allowed. Be sure to start your day with a satisfying breakfast that is hearty but won’t make you sluggish: fruit, grains and yogurt are great choices. Also, be sure to print out a trail map from Cook County Forest Preserve web site, so you can be sure you get to visit as many great little scenic stops along the way. On that tangent, bringing a camera along isn’t a bad idea, either! There is just so much wild life to capture along the way, including deer!
Either load your car with your bikes or ride the buses or Metra train in, making your starting point at Caldwell woods. There is plenty of street parking in the surrounding neighborhood, which is very safe and pretty, so no fears there! Simply load up your gear, just on your bikes and go! If your bikes are built with a little gravel and dirt in mind and your bodies are up to it, go ahead and opt for the unpaved ones! You’ll get a much better view of the natural landscape, and yes, it’s much less used! In my opinion, the Yellow Trail is the best, because it tends to follow the river the most, and since other folks like it too, it’s more paved than the others. It also happens to go right through the Skokie Lagoon, it taps all the bathroom breaks, and it will lead you right to the Black (paved) Trail, heading right for Botanical Gardens. Now speaking of bath rooms, the last one until the gardens is a little before the overpass, so be sure to keep that in mind!
Once you get to the gardens, be sure to invest at least a couple hours there. There are plenty of spots to lock up your bikes, and hey – you can even ride a tram if don’t feel like walking! And yes, there is a snack shop and cafe inside as well, in case you’ve already depleted your food supply or want something a little different. Just remember to fill up your water bottles before you leave!

Forget the other trendy sushi places in the loop. Come to Sushi Loop, a restaurant that’s all about the food, not about the glitz and glamour. Located, strangely enough, in the heart of Greektown, this unassuming sushi house serves your favorites in a pleasing, casual environment.
No matter what time of year it is, there is simply no better place to stop to smell the roses, or any other flower for that matter! And in February, there is no better place to kick start Valentine’s Day than to visit the conservatory for chocolate tasting! Of course, because this place is encapsulated within beautiful glass walls, any time of year is a great time to go, and its proximity to city dwellers makes it a great place to go!
While not as visually appealing as many of other Greek restaurants in the up-and-coming Greektown area, Mr. Greek Gyros has something to offer everyone who’s hungry and is looking for better-than-average portion sizes. Stripped of the glam and glitz, this corner diner has the feel of a greasy spoon but boasts a flavorful menu that makes you think twice about judging a book by its cover. In an area literally surrounded by other Greek restaurants, Mr. Greek Gyros stands out thanks to its large glass windows, which give you a peek inside, where you’ll see a plenty of seating and a huge menu above the counter.
Wicker Park residents are known for their hip, trendy clothes. But who would have thought that in a big city like Chicago, you could find all the latest trends at a consignment shop? At Lenny & Me on Milwaukee Ave, you can do just that. However, upon stepping in, you might not even realize you’re in a used-clothing store.
For a good date in Wrigleyville, pass up the noisy sports bars and meet at Uncommon Ground on Clark Street. The restaurant has two bars, a big one in the front and a smaller one in the back. It offers coffee drinks as well as beer, wine and cocktails and a menu from breakfast to desserts from Bittersweet Bakery. Your date may be impressed with the organic, seasonal menu and both meat-eaters and vegetarians can find tasty dishes here.
Sometimes my plan for a girls’ day out centers on cake and coffee rather than cocktails. For a sweet treat, take your mom, sister, best friend or any chocoholic or coffee aficionado to Julius Meinl’s Café.