Cycle around Lake Michigan on a bicycle made for two – book online and get your bike for a whole half day for $35… or if an hour is more your thing, the $20 fee will leave you with spare for ice-cream afterwards! See here for details.
Go see a Cubs game and eat some nasty baseball hotdogs.
Head to Sweet Mandy B’s for some old-fashioned cupcakes and coffees. The Dreamsicle is to die for, and they even sell Smores!
Escape the wind by heading to the humidity of the Lincoln Park Conservatory and be transported to 3,000 square feet of tropical paradise that you can stroll around in. Your very own garden of Eden.
Go get a half-size grand seafood platter from Frontera’s and get messy slurping oysters and cracking shells.
Head to Vosges Chocolates at Lincoln Park and gorge yourself full of weird gourmet treats. Anyone for a bacon-filled flying chocolate pig? Chilli brownie? Lemon, lavender and white chocolate cocoa?
After you’ve eaten dinner at home, head to Geja’s Cafe for a romantic fondue and snuggle in a dark booth while a flamenco guitar plays in the background… the flaming chocolate fondue is perfect for a Dessert Only date! Alternatively, the Gruyere cheese also comes in under budget!
On a Thursday or Friday in Summer, indulge in some culture and live music with free entry to The Art Institute of Chicago. Some of the world’s most famous and oldest paintings are held right here in our city! When was the last time you saw them? Get arty in your interpretations of works with your date.
Monday nights at the verry romantic Juicy Wine Company means $5 Mojitos and Cubano sandwiches all night! Go immediately!
A corny, fun night at Ed Debevic’s... get a milkshake with two straws and some burgers while watching the all-singing, all-dancing wait staff perform the old tunes. Very cheesy, great for laughs! Grease is the word!
Download this self-guided tour for the Skokie Northshore Sculpture Park and take a stroll together to admire 2 miles of contemporary sculpture art!
The Museum of Contemporary Art is FREE every Tuesday, all year round, and open until 8pm. They also run guided tours through the day... drop past the cafe with your honey for a light snack and coffee afterwards!
The National Musuem of Mexican Art offers free entry every day of the year! Explore Mexican culture, from the ancient to the contemporary with authentic textiles, sculpture, paintings and photography to name a few!
Free entry, always, to the Museum of Contemporary Photography where the collection includes works by the iconic Andy Warhol, along with other masters of photography... well worth a look!
It may sound touristy, but when was the last time you watched one of the night shows at the Buckingham Fountain? Every hour, on the hour, from dusk it's a spectacle of water and lights! Then take your date for a glass of wine or a hot chocolate at a nearby cafe.
Parks all across the city offer free Movies in the Park from sundown, June - September. Pack a picnic and take your sweetie with you to enjoy a film under the stars...
Be big kids at Amazing Chicago on Navy Pier! This indoor maze and entertainment centre is a stack of fun, if you don't take yourself too seriously! Chase each other through 4000 sq ft of tunnels, mazes and spinning rooms. You might get dizzy! You'll laugh lots.
Movie night every Tuesday and Wednesday at the Butterfly Social Club - organic specialty drinks, popcorn, free food... what more could a loved-up couple ask for?
Take your pooch with you for date night on Wednesdays at Joe's Bar! Doggy Happy Hour on the outside terrace means treats for the pups and great drink specials for the humans. Then take puppy for a run in the park on the way home and play together as a family.
If you like good, dirty fun then Dirty Bingo at Victory Liquors is perfect! Giggle the night away at filthy jokes! Bingo board will cost you $10, with additional boards $1 after that. Comes with a free drink and $4 martini drink specials all night. Fun! Every Thursday.
Take your sweetie for a poker lesson at Poker School 101, every 1st and 3rd Tuesday of the month at Citizen Bar. The lessons are free, the wine is half price and the sun will be shining on the rooftop terrace!
Take a walk through Graceland Cemetery Sounds creepy but it's not. Take your date through the peaceful surrounds, there are rolling paths, really old trees, the greenest grass and the most awesome wired fences around. Very cool. (4001 N Clark St, between Belle Plaine Ave & Irving Park Rd, Chicago)
Take your date to a sing-a-long at Rory Lake's Karaoke Dreams Rory makes sure everyone has the chance to sing. After a few drinks you'll both be up and dancing too. They have relatively cheap cans of PBR and Modelo for $2 and $3, respectively. You will have a good time!
Have a picnic at Garfield Conservatory! Garfield Conservatory is very peaceful! The rooms are teeming with foliage, little footpaths, colorful flowers and turtles too! The central room has a very large pond with koi fish! Entrance is base on donation!
Nature at its finest at Lincoln Park Alfred Caldwell Lilly Pool This place is a little hidden gem. You can hunt down a sunny silent spot, soak up the rays, listen to birds. Find a spot to sit and stare into the beautiful pond! The place is really romantic. The best thing is its free. (Fullerton Pky and Cannon Dr, Chicago)
Be a kid once more at Chic-A-Go-Go You will have to get a costume and dance along with kids, college students, older folks and other friendly people with an upbeat music. It's pretty crazy but you'll have heaps of fun! Free Snacks, Free admission!
Beer n Date at Bernice's Tavern Their beer selection is large and includes some Lithuanian and Czech beers for different palates. Drinks are cheap, only $3! Jukebox is free!
Spend a day at Promontory Point! The place is right on the lake, the views are stunning! It's a great place to chill out, take a picnic basket for the perfect date out. (5491 S Shore Dr, Chicago)
Take your date to see the animals at North Park Village Nature Center Stroll around the place and you will see deer, bright yellow spiders, tadpoles, turtles, grasshoppers and tons of birds! Step into a forest of wetlands in the middle of the city. You can borrow binoculars for Free! (5801 N Pulaski Rd # C, Chicago)
Go to Chocolate Shoppe Ice Cream! The place looks like someone blew up an ugly purple prom dress and a barrel of Crayola crayons. You'll feel like a kid eating an ice cream! They have cones and waffle bowls adorned in M&M's, candy coating, peanuts, etc, drizzled in white or dark chocolate. What a treat!
Take your date to Jay Pritzker Pavilion Be surrounded by beautiful music & the beautiful city! They have a amazing sound system, lush grass and the incredible perspective of the city from the lawn at dusk. And best of all it's free! (201 E Randolph Street, Millennium Park at Stetson Ave, Chicago)
Blues at Blues R & B For a $10 - drinks are strong and the music is really good, it is one of the best places to make you feel proud that you live in Chicago. It's small, intimate, no frills, a genuine hole in wall.
Play golf at Novelty Golf & Game Room only $15 for 2 people! Old school miniature golf at its best. Most holes involve a moving apparatus and you have the opportunity to win a free game when returning your ball.
Hotdogs at Hot Doug's Try the Smoked Gouda, Apple-Chicken-Sausage and a side of Chili Cheese plus soda for only $10. They also have regular hotdogs for only $1.75 and they taste awesome. Combine this with another date.
Introduce your dog to your date at Humboldt Park It's a dog walkers dream. They have multiple paths through out the park that wind around a lake, tree glen and open fields! They also have tennis courts if you fancy a hit. Great views of the city as well. (1400 N Sacramento Ave, Chicago)
Laze around with your date at Grant Park The grass is lusciously green and the fountain is the coolest part. The place is huge! Have a picnic, take your dog, or look at the beautiful views of the Chicago skyline. (331 E. Randolph Street at Columbus Dr, Chicago)
Dine at Birrieria Zaragoza Try the Birria (a spicy Mexican goat stew) is the specialty of the house here. They also have awesome salsa and homemade tortillas that they add to have that extra authentic feel to the food An adult portion will run you $8.50, plus at least $3.00 for some salsa to share. (4852 S Pulaski Rd, between 48th St & 49th St, Chicago)
Go to Tony's Italian Deli and make an Italian Picnic This place serves everything Italian, including pizza breads, salads, and pasta dishes. The best food is the sub. There are some cold subs for as low as $4.99 for a 15" or $2.99 for a 6".
Catch a flick at Gene Siskel Film Center! Tickets are fairly priced at $10, and it's less for a student. There's also a membership card you can get which gets you $5 tickets. It is a place to view the truly non-mainstream flick or the foreign film du jour, this is the spot.
Eat at Dragon Lady Lounge, Korean Buffet on Thursday nights It's only $9.99 all you can eat! A glorious selection of pan-Asian food: fake-chicken dumplings, sesame sauteed vegetables, spices, rice, perfectly marinated tofu, crispy home-made veggie burger balls and so on. (3188 N Elston Ave, between California Ave & Belmont Ave, Chicago)
Go and see the traveling circus when its in town! Try to resist the urge to run away with it and become trapeze artists!
Make it a Miko's Italian Ice Date in summer. A combo is 2 flavors in a cup, $3.50! Pig out in a park... banana chocolate chip Italian ice is my favorite flav!
Track down Cevapcici Chicago via facebook as they only appear at festivals... a Croatian delectable delight. Treat your date to an ethnic wonderland. Not to mention that you'll be at a festival at the same time. Everyone loves it. Priced at $6!
Hit the Beach - the Kathy Osterman Beach. The entire beach is beautiful and warm and it gives off a very welcoming feeling! Clean sand and quiet breezes and the water is clear.
Enjoy music at the Velvet Lounge. Cover charge is $15 and you can even bring in food! There are shows here five days a week, and if you are a jazz or live music enthusiast a visit to the Velvet Lounge is a MUST.
History lovers - take your date to the Oriental Institute Museum! The place is bigger than it looks! It is jam-packed full of artifacts including 3 mummies! It really is a terrific collection and it is for free! Or suggested donation of $5!
Tour Rosehill Cemetery & Mausoleum! Sure - its a little weird, and seems spooky touring a cemetery but this place is pretty amazing. There are some graves over 200 years old and exquisite sculptures! There is a FREE tour of Rosehill Cemetery at 10am on the 2nd and 4th Saturdays each month, fabulous!
Enjoy Beautiful day and night views at the Millennium Park. You can lay on the grass on the Pritzker Pavilion and relax. Or you can view the architecture of the stage which is simply breathtaking with the cityscape in the background. The gardens are beautiful as well.
Check out this amazing place - Hungry Brain! They have a jukebox with a great music selection! Good beer, get a bottle of Dogfish Head for $3.50. They have a small low key atmosphere! Coolest dive bar there is! (2319 W Belmont Ave, between Clybourn Ave & Oakley Ave, Chicago)
Bake a cake together... FROM SCRATCH! Get creative and get messy. See what amazing creation you can make!
Great food, full tummys at Zaleski & Horvath MarketCafe. For $30, you will have, Blue Moo: roast beef, bleu cheese, red onion, tomato, mixed greens and mayo on French bread. Smoky & O'Malley: a panini with smoked turkey, brie, curried mayo, tomato chutney and romaine grilled on wheat. Plus the 2 lovely lattes and a slice of Tasty lemon pound cake.
Visit Old St. Patrick's Church. The church has an old fashioned structure with bell towers. It has a colorful and uplifting interior and an austere and impressive exterior, this church is 100% amazing. The fine details in wood work and paint to the beautiful stained glass, this church is off the charts.
Dance at Big City Swing! For only $10, you will have a one hour lesson of Balboa and 3 subsequent hours of feel free swinging! Definitely a great alternative to the usual weekend night activities!
Date n Plate Combo at Taza. Combo Plate come with 2 mini skewers of Kifta (beef/steak) and 2 skewers of Chicken Schawarma, dill rice and a small side salad and half a pita bread. Only for $7! Falafels are 50cents each. (176 N Franklin St, between Monroe St & Couch Pl, Chicago)
Try a Polish dish at Paul Zakopane Harnas Restaurant. For only $10, you get to have a Polish combination platter. It includes sausage, pierogi, stuffed cabbage, meatball, potato pancakes, and sauerkraut! Plus soup, salad, loaf of bread and dessert! It is one of a kind!
Try Israeli food at Hashalom Restaurant. Cheap n' cheerful food. Try the $5 Israeli combo plate appetizer. It has a kefta in salsa plate, and a kefta kebab. It is so yummy! (2905 W Devon Ave, between Francisco Ave & Richmond St, Chicago)
Baklava Heaven at Nazareth Sweets. They have trays and trays of fresh baklava - YUM! 8-10 baklavas for only $3.50!
Chill out at Star Lounge Cafe. They have a backyard patio... the place is comfortable, cozy. They've got really large coffee like the large Mayan Mocha (spicy) - 20ounces costs $4.50!
Lunch date at Potbelly's. The sandwiches are hot and freshly toasted. A sandwich and cookie is $6! The sandwiches are unique and the cookies are delicious and chewy and full of chocolate goodness!
Best Grits at CJ's Eatery. Try a catfish, 2 eggs, 2 biscuits and shrimp grits for only $10.95. The grits are tasty, good, meaty, selections of bacon, cheese, delectable cream and winse sauce with lightly cooked shrimp, tasty pan toasted buttermilk biscuit and perfect over easy eggs! Amazing!
Efebina's has everything a good coffee shop should have - perfect for a date. Their coffee, espresso and teas are always delicious. Muse with your date while munching down a bagel. (1640 S Blue Island Ave, between 16th St & 18th St, Chicago)
Take your date to BIG & little's, a clear winning dish = Fish tacos $3 a piece, fresh tilapia, perfectly cooked, flaky and flanked by red cabbage, tomato, onion and a spicy sauce combining chipotle and mayo. This restaurant is little with a big taste! (939 N Orleans, between Walton St & Oak St, Chicago)
Get refreshed at Mario's Italian Lemonade. Lemon, watermelon, cherry, peach and so on for only $1! (1068 W Taylor St, between Carpenter St & Aberdeen St, Chicago)
Make your way to the woods at Caldwell woods. An awesome forest! Roam around on bikes - this place is so huge, a picnic is a must. You find winding paths that disappear into the woods perfect for a great make out session!
Try finger-licking goodness at Wings Around the World! Get crispy, thin, delicious, seasoned fries and a drink all for $15 plus 20 Wings! Chicken wings are a real treat, they have sweet, sour and spicy sauces to choose from!
Bhan Mi in Nhu Lan. Bhan Mi, a Vietnamese sandwich on French rolls. They offer many other Banh Mi including the bbq pork, the chicken and the pate. Also try the pork belly sandwich - $3.25 each!
Meet up for coffee at the Bridgeport Coffee Company. Enjoy a decent meal, a great sandwich and a coffee for less than $8! (3101 S Morgan St, at 31st St, Chicago)
Take your date to Piatto Pronto. Their sandwich has fresh mozzarella balls, tons of deliciously sliced prosciutto pile on high on a crispy loaf of bread covered with sun-dried tomato and basil. Six inches for only $5! But it is bigger than 6 inches, you'd be wondering how big their 12" is!
Smoked shrimp at Calumet Fisheries! The smoked shrimp is the pride of this place! It is large, shell on & super crispy! It is only $8.99 per pound! Also, try Cole Slaw ($0.49/cup) - served in a takeout plastic sauce container, finely diced, mayocentric goodness!
Have fun at Shoes Pub. Shoes is a great place to have fun and do karaoke on a Friday night! They have a pool table which cost $1.50 per game and darts which is free! (1134 W. Armitage Ave, between Clifton Ave & Seminary Ave, Chicago)
One of the brightest parts of Chicago's winter " ZooLights at Lincoln Park " returns in late November. ZooLights is free and open to all. In addition to the one million lights, watch professional ice carving demonstrations, ride the carousel, and visit with Santa! Wrap up the evening by warming up at one of the many local coffee shops or head over to Hot Chocolate in Wicker Park/Bucktown!
Go Check out the Map Room and then grab a bite to eat at Feast. Amazing food, good atmosphere. :)