"Three square blocks of open lakefront complete with an outdoor music pavilion." With the giant bean, multiple gardens, a fountain play area, an ice skating rink, a cafe, statue art, and more, it's easily one of Chicago's most popular sites. Not to mention, if you walk toward the lakefront, you'll also see the gorgeous Buckingham Fountain, which features a colorful light show at night! For some great outdoor activities with your family or alone time with your partner, this is an ideal summer/fall scene!

Free on Thursday and Friday evenings, "this Classical Renaissance structure, guarded by two bronze lions at its entrance, boasts one of the world's great art collections, including the trademark "American Gothic." It's the perfect leisurely way to spend a nice morning or afternoon. Amazing restaurants are located on site and the gift shop is a guilty pleasure, indeed! Enjoy a cultural experience and then meander outside to Millennium Park for a stroll in the gardens.

The Chicago riverwalk is an excellent way to see the city, have some time to yourself, and get some exercise if you like walking or running. The river flows through the heart of the city and I often call it the artery of Chicago. If you follow it through the entire city, you get a sense of the pulse and character of home-sweet-home Chicago. We also recommend a boat tour! That's an excellent way to see it and get some information about what you're looking at. I have taken 3 boat tours even when I lived in Chicago, because the views, the history, and the architecture are simply breathtaking. It's also the most relaxing way to see downtown if you're tired of walking. Click here for the recommended boat tour I have taken with my family and friends!

"This main downtown thoroughfare includes the Magnificent Mile, a stretch full of every store imaginable and several of the city's landmark buildings." It's an absolute shopper's delight and a PHENOMENAL walking tour of Chicago - for free! You can actually start at Millennium Park and walk all the way to the Drake Hotel/Oak Street Beach. It's a guaranteed splendor of parks and public art on the southern end and major department stores, specialist shops, and historic buildings toward the northern end after the river. But don't stop there! For the adventurer in you, let yourself enjoy the beautiful Gold Coast lakefront walking path along the water that continues all the way up to Northwestern University.

"The largest science museum in the Western Hemisphere! Housed in the only remaining building from the 1893 World's Fair, MSI is a Chicago must-see. You'll experience 14 acres of hands-on exhibits and have the chance to stand before a 40-foot tornado; climb aboard a World War II German submarine; take a run in a human-sized hamster wheel; descend into an Illinois coal mine; tour a fully functioning eco-friendly home; board a 727 hanging from the ceiling; transmit your pulse to a 13-foot, 3-D beating heart; and much more! MSI is not a place where you walk around quietly and observe. No way! You get involved in the fun—and learn—by doing. Just a few miles from downtown with convenient underground parking."

"Navy Pier is the place where all of Chicagoland and tourists from around the world have come together since 1995 to enjoy the beauty and the thrills of a day on Lake Michigan. From rides to restaurants, exhibitions to entertainment, shopping to dining cruises and tour boats Navy Pier has it all - in a location unlike any other! There's so much to do in our 50 acres of parks, promenades, gardens, shops, eateries and attractions.Take a ride on our 15-story Ferris wheel. Catch a movie at the IMAX® Theatre. Visit three floors of hands-on fun at the Chicago Children's Museum inside the Family Pavilion. Experience any one of the cruise boat rides departing from Navy Pier's South Dock. Or just kick back and enjoy your favorite form of entertainment at the Pepsi Skyline Stage, Dock Street Stage, Landshark Beer Garden or Family Pavilion Stage.Come experience all that Navy Pier has to offer year-round!"

"No trip to Chicago is complete without a visit to the top of the tallest building in the Western Hemisphere and The Ledge at Skydeck Chicago! Treat yourself to a "one stop Chicago" experience on your journey to the 103rd floor. Enjoy 360-degree views spanning up to 50 miles and 4 states and our most spectacular view - 1,353 feet straight down! "Dare to Stand Out" on The Ledge - glass balconies extending 4.3 Feet outside the building provide a thrilling, once in a lifetime experience!"

"Home to the Lincoln Park Zoo, this popular park is also located in a neighborhood called Lincoln Park...There are various playgrounds, walking and biking paths, a restaurant on the north side and even a free zoo. One cannot get bored here!" This area has an expansive outdoor feel well as a TOTALLY unique neighborhood that's tucked away just behind it. Lincoln Park is the hub of northern Chicago culture and your eyes will constantly lure you into new, fun shops, restaurants, and other areas to explore. Trip Advisor is correct. You CANNOT get bored here, but you might get hungry. So, duck into a cute little restaurant nearby when you get a chance!

Wrigleyville is home to Wrigley Field and the area is vibrant and loyal to its World Series qualifying baseball team, the Cubs! You may know that the Sox and the Cubs represent the south side and north side of Chicago. Adam and I are fierce Cubs fans! So much so that we attend every game we can when they're playing the Giants in San Francisco, and Adam plans his vacations for when the Cubs are in town :-) This is a cool area to explore if you've never been to Chicago. Between the amazing historic baseball stadium and the tons of bars, restaurants, and shops, you'll quickly fall in the love with the hustle and bustle of this northern part of Chicago. It's also somewhat Lake front adjacent, just 6 or 7 blocks away!

This is a FANTASTIC 3-day doable list of restaurants, shops, and activities to do while you're in town for a brief visit. Adam and I can vouch for Diana R's researched choices of where to go, what to eat, and what to see to get the most bang for your buck! We HIGHLY encourage you to try some of her suggestions. Gino's East, Howl At The Moon, Water Tower Place, and She'd Aquarium PLUS Pizzeria Uno and Due (they're the same).

Cleverly named, this is the closest you can feel to Italy in the middle of skyscrapers. This is one of our treasured date night spots. If you love food, and I mean LOVE food, you're pretty much guaranteed to find paradise here! It's the most satisfying combination of an old Italian market, a classic gelateria (ice cream), a scrumptious cafe, an excellent beer garden, a decent wine bar and cellar, a well-stocked Sur La Table-esque cooking supply store, and several phenomenal Italian restaurants that each have ONE cuisine they specialize in serving: fish, pasta, pizza, aged meats and cheese, or meat. The products sold are authentically Italian imported and the experience of walking through alone is worth the trip. It's a deceptively EXPANSIVE hidden gem of rustic-meets-modern influence in the middle of downtown...and it's down the block from Pizzeria Uno and Due!

This was a favorite date night spot for Adam and me. Coincidentally, it is our favorite pizza place in the city and honestly, you've GOTTA GO AT LEAST ONCE! It's a long wait to be seated, so plan on putting your name in and coming back in an hour. However, the deep dish pizza is absolutely perfect to our native Chicago tastebuds. The crust is incredible, the sauce is homemade, and the different layers of flavors will leave you in the best food coma you've never had. Prepare yourself for a thick slice of heaven! If Pizzeria Uno is busy, just walk 100 feet down to it's sister place Pizzeria Due. They're absolutely the same quality food!

Pizza is a complicated thing in Chicago. Everyone has a different opinion and everyone is right (or else!) Lou Malnati's is very famous, but in our humble opinion? It's very good pizza if you've never tried Chicago style pizza. People highly review it all the time. We put it on here, because you could very well love it, and we would never want to deprive you of that experience! ...But we just in case it's too busy there or you have to chose, we gave you another option for Pizzeria Uno, and that's our favorite :-)

Home of the White Sox and Obama for a while! Often called "The Culture Coast", it's rightly named because THERE'S TONS to do and experience on the Southside and it doesn't get enough credit for the flavor and character is gives Chicago, as a whole. The more public tourist spaces are really rich in culture and history. #5 (Nightlife) is filled with amazing opportunities to have a blast on both Bourbon Street and Western Ave for the evening.!

The Chicago Traveler says: "The Southside of Chicago plays an important role in Chicago's economic and cultural life. With its Industrial Park being one of the most successful in the city, the Southside contains a diverse, hardworking population. There's a lot to love about the Southside of Chicago, from historical buildings, a great variety of restaurants and museums, to theater and sports. The diversity of the Southside's population ensures there is a lot to do, no matter what your interests are." Just be mindful of the places you choose to walk around or visit at night. Make sure they're more populated and busy. The news doesn't lie about personal safety plummeting after sundown, especially if you're a tourist. But that really goes for all of Chicago.

A museum dedicated to African-American history, art and culture, this space encapsulates the rich history of a beautiful and strong people. It has this interactive exhibit of former Mayor Harold Washington, and many other interactive exhibits that kids and adults thoroughly enjoy. It's not usually very crowded or busy, which is sad because it offers such a great afternoon's worth of fun activities and learning. But it's off the beaten path from the more touristy places. My mom and I loved going here when I was younger, and we hope that you enjoy this informative, eye-opening treasure, as well.

"As the art museum of the University of Chicago, the Smart Museum of Art is home to acclaimed special exhibitions and a permanent collection that spans five thousand years of artistic creation. Free and open to the public."

Their mission is: "INVITING EXPERIENCES. SPARKING CONNECTIONS. Through a mix of creative partnerships and ambitious educational programs—from K–12 initiatives to lively art-making programs for families to provocative lectures and symposia—the Smart Museum strives to connect visitors of all ages and backgrounds with the full spectrum of the visual arts." LOVE THAT! The exhibitions are also often a welcomed escape of creativity, introspection, and enlightenment, or "food for the soul" as my mom puts it. University of Chicago's art museum is both an "adult place" AND a family-friendly place. As advertised on their website, they warmly invite you to: "Drop by and join in the Smart's free family activities every month! Each Family Day features hands-on art activities designed to inspire children to think about and respond creatively to art and the world around them." Check the calendar to see if their family day the month of our wedding lines up with your trip!

"Art and history museum located on the campus of the University of Chicago." Such simple terms describe a 'not-to-miss' experience in Chicago's Southside's Hyde Park. This intellectual and historical experience is easy to get to via CTA (public transit) and admission is FREE! As Chuck A. stated: "The Oriental Institute has an amazing archeological collection from the Middle East as well as complementary educational programming. It is great for people who are interested in history or other aspects of culture. The presentation of the collections, however, is very academic and somewhat dry. It is great to combine a visit here with Frank Lloyd Wright's Robie House, the Smart Museum of Art, and/or the Osaka Gardens nearby." He's right, but this museum is worth it alone to see the huge mummy of King Tut, the gigantic winged bull, and the large stone wall reliefs from Mesopotamia.

For those of you who would like to know what else the city has to offer aside from our shortlist, Trip Advisor has vetted through the millions of options and left you with ONLY the best of the best. There are 19 pages of adventures just waiting for you! Click on the website and explore for yourself all the AMAZING and fun things to do in Chicago, and just be aware of the dates, times, and prices of some of the suggestions. Whether this is a vacation or a staycation, you will have plenty of opportunity to explore the city or fall in love with it all over, again :-)

This was a favorite date night place of ours and dear to Adam's heart, because of his Cuban heritage. They do brunch and lunch, too. If you're willing to drive in to the Northside of Chicago, the food is ALWAYS worth it. It's authentic and super flavorful. We loved the whole red snapper, the croquetas, and the Cubano sandwich.The ambience feels lively and fun, with great latin music to set the scene. The restaurant itself has an al fresco option with a lovely little patio area lit with strings of lights hung across. It's a great family place, but also the perfect date night opportunity. Prices are very reasonable, cheap in some cases. Expect to be very satiated and very happy!

This is the perfect brunch/breakfast place, especially if you have a hangover - which you might since our wedding has an open bar! This CASH ONLY menu alone speaks volumes! The food is spectacular and the service is great whenever my friends or I go! It also features vegetarian and gluten free options that are simply scrumptious, I've heard. Personally, I prefer meat and gluten with my breakfast lol. So, I would go for the "numero 6" which is a steak burrito with grilled skirt steak, organic eggs, onions, potatoes, and cilantro. The corn arepas with chorizo or any type of omelet is also delicious. The biscuits and gravy and the chilaquiles are yummy, too. Honestly, it's really hard to make a bad choice here. It's all good! Lastly, they have good, cheap, alcoholic drinks. Enjoy!

Petterino's was where we had our FIRST date! It's in the heart of the theater district, just a around the corner from the Goodman theater. (Side note: That's where my mom performed, in her heyday, when she was getting her Masters in Theater!) It's practically dripping with history, Chicago character, and hollywood's golden touch. For decades, famed actors and actresses have graced the booths and bar stools of this Italian establishment...and they've also signed their pictures on the walls, too! Its dim lighting, large comfy seats, and wooden structure make you feel right at home in this God-father-esque restaurant of choice! It's a bit on the expensive side of things, but it sure was a treasured beginning for us! We hope you stop in for a drink or stay for a meal. It's quite a treat!

Located in the Hotel Lobby of the W (City Center) Hotel, The Living Room offers a cozy, trendy vibe. "Our Living Room is a place of cathedral-like dimensions and cabaret-like distractions. Daydream under the vaulted ceiling or head up to Plateau for munchies, cocktails and a sexier ambiance. Have a cozy tête-à-tête at a table for two or go for glam on the diva couch." For a night cap, this place is PERFECT! Drinks are about $15 a pop, though, so we recommend it as an end of the night deal. It was such an unexpected treat for the senses between the decor and the drink selection. We were so impressed with the mixologist. He had 20 years experience and STILL experimented outside the box with different drink combinations. Creative genius! It's a great place to just chill out and enjoy each other's company before your date's over :-)

This was another date night spot for us and it never disappointed! The food menu is expectedly on par with high French American standards (be ready for a rich, heavy, hearty meal), but the drink menu is truly an adventure for your palette! It's about $15 a drink, but worth it! Their selection is fewer than you'd expect, but I recommend the French Gimlet, Aviation, and French 75. We LOVED trying all the different kinds of drink concoctions and the ambience is cozy, charming, and inviting. We recommend this for a nice couple's evening.

It's a fun little spot with darts, a touchtunes juke box, digital trivia games, and a great selection of beer. The food's not half bad, either! It's what most might classify as a 'dive bar' and it oozes character and puts on absolutely no "airs". This place holds a very special place in Adam's heart, because he spent almost every night he possibly could (while we long distance) with his friends here. They're actually in the bar in the picture featured here. Rick's was where he went after trivia nights Tuesdays or Thursdays, after work on Fridays, with me sometimes, after studying or exams, most Saturday nights, pretty much any night of the week....not Sundays, though, because it's closed on Sundays. Their picture is on the "wall-of-fame" in the bar, because Adam and his friends were such dedicated patrons, before they left. It's definitely a neighborhood hang out and a nice, down to earth gem in the West Loop area.