Best Date Ideas for Chicago Singles

The Windy City…. Chicago. This city is another one that immediately puts images in your head. There is a lot to do and a lot to see. When looking for what to do with your next date things could get a little overwhelming in a city like this. That is why we have given you our list of the best date ideas for Chicago singles. Whether it is your first date or your 33rd anniversary we have a list of places to go. We have divided the list up into 4 categories: restaurants, bars/lounges, comedy clubs, and sweet shops/bakeries. Browse and enjoy! You will find something no matter the occasion.

Restaurants
Bars/Lounges
Comedy Clubs
Sweet Shops/Bakeries
Helpful Blogs

Best Restaurants in Chicago

Whenever someone is trying to figure out what to do for their next date they will ask friends, family and everyone else they know. Grabbing a bite to eat is one of the most common suggestions. Well, there are tons of different types of places to eat, so narrowing it down to the one perfect place can be tough. It is important to pick the “best fit” restaurant because it gives of a certain impression as to the type of person you are. Below you will find our list of the best restaurants in the Chicago area. All of these restaurants are truly top-notch, find the one that fits your next date!

Photo via Sheraton Hotels and Resorts

Goosefoot – This restaurant is located in Lincoln Square and is headed up by Chef Chris Nugent. Here you will find fine contemporary American cuisine that is created from an artful blend! You will not regret coming here.
Next – Here is a different type of restaurant…. Next only take presale tickets helping to eliminate no shows and increase predictability. You will be sure to leave satisfied if you dine here, just make sure to plan ahead.
Tavernita – This restaurant is a sexy and modern dining experience giving you foods from Spain and Latin American flavors. Here you will find the right foods to spark of the conversation with your date.
El Ideas – Elevated Ideas in Cuisine and Dining is the brainchild of Chef Phillip Foss. Here you will get contemporary cuisine in a setting like another other. The setting is more laid back as the dining room only holds 16 seats and is found in the kitchen. You will be sure to have a great experience here!
Perennial Virant – At Perennial Virant you will find great cuisine and a good environment to relax and eat in. Whether it is brunch, dinner, dessert or a cocktail you will leave satisfied here.
Vera – Here you will get Spanish cuisine and worldly wine…. That will equal an amazing dining experience. Bring that special someone here for your next date!
Acadia – Acadia is headed up by Chef Ryan McCaskey. Here you will get a blend of contemporary and classic cuisine that will leave you refreshed and satisfied.
Yusho – “The door is open and the grill is hot!” Definitely a true statement when talking about Yusho. Come in with your next date and enjoy this great atmosphere and great food.
Au Cheval – Here you will get classic house-made dishes, but with a creative twist. Bring your next date into this cozy atmosphere and enjoy some great food!
Ada Street – Come in and enjoy Ada Streets bar! Walk-in’s are welcome! Bring your next date in for a relaxing atmosphere and fantastic food.
Libertad – Looking for some great Latin American food?! Well stop on by Libertad and enjoy some fine cuisine! You won’t regret it
Ombra – Looking for a great Italian Bar?! Ombra is where the casual comfort of the neighborhood meets the energy of possibility.
Autre Monde – Here is a top notch place to enjoy some great food and a comfortable atmosphere. You will be sure to enjoy your next date if you bring them here!
Rustic House – Rustic House is located in Lincoln Park. Here you will find a cozy environment and wonderful food.
Slurping Turtle – Looking for a place where slurping is acceptable? Well, this is your place…. The food is so good you will be slurping in delight!
Urban Union – Are you looking for somewhere that is classy, but comfortable? Well, this is your place! Don’t be afraid to take your next date here.
Grange Hall Burger Bar – Looking for that perfect burger to chow down on?! Well, this is your place to grab that delicious burger and get your grub on. You won’t regret it.
Bar Toma – Chef Tony Mantuano is the brains behind this operation. This is your neighborhood pizzeria and bar. There is a ton of variety that will keep you coming back time and time again leaving you more than satisfied every time.
Nellcote – Nellcote provides you with variety! Enjoy some fork and knife pizza, a cocktail, or some of their other fantastic food.
Charlie Trotter’s – Charlie Trotter’s is coming up on a big celebration…. 25 years. They offer you two services. A sit down restaurant and Trotter’s to go! Both are fantastic options. So, either come on in and sit down and enjoy a meal OR come on in grab some grub to go and enjoy it in any location you choose.
Stefani Restaurants – Stefani provides you with 10 options to keep you entertained! No matter the occasion Stefani’s got you covered. So, just check out the options and see what will work for your next date.
Frontera Grill – Frontera offers Chicago with an authentic Mexican grill. So, if you’ve got a hunger that can only be tamed by the some great Mexican food this is your place!
Harry Caray’s – Baseball fans in search of a great Italian steakhouse and bar, look no further. Here you can satisfy your appetite for baseball and steak!
Boka – Chef Giuseppe Tentori is the man behind this fantastic restaurant. Here you can enjoy a number of different types of seafood!
Rosebud – Rosebud Restaurants offer you a number of different places for you to enjoy great food and a great atmosphere. No matter what type of restaurant you are looking for Rosebud will be there to fill the void!
Spiaggia – Tony Mantuano is the mastermind behind this top notch Italian restaurant. So, if you are looking for some quality Italian food look no further.
Keefer’s – Keefer’s has been raved by many as a great place to get a steak or seafood. The Food Network, Playboy Magazine, and Crain’s are a few that have given these mentions. You can’t go wrong with Keefer’s!
Blackbird – Here is a classy, modern, fine dining experience like no other. If you are looking to impress your next date then look no further.
Leona’s – Looking for something a little bit more old school? Well, here ya go! Leona’s gives you a classic feel with great food!
Ria – Ria is a classy, modern restaurant! If you are looking for somewhere to impress your next date, this is the place!
Chama Gaucha – Looking for something a little bit differen?! Check here for a great Brazilian Steakhouse. You will be sure to leave happy!
Perry Street Brasserie – Perry Street provides you with casual fine dining! So, if you are a wanting some great food, but without having to get overly dressed up this is your place
Tru – Looking for a restaurant that has a little bit more than great food?! Well, Tru has not only great food, but they add is some fine wine and art to their fine cuisine. You will not regret coming here!
Girl and the Goat – Girl and the Goat gives you fun foods, craft beers, and their own wine! If you’re looking for a unique and fun experience you will be sure to get one here.
Vie – Chef Virant is the man behind the food here. He provides you with fresh ingredients for all of his seasonal contemporary American cuisine. “Tastes of the Season, preserved” sums up what you will get when you visit this restaurant.
Gaetano’s – Chef Gaetano Di Benedetto is the brains behind this amazing restaurant. This is one of 600 restaurants who have gotten the seal of “Authentic” Italian restaurant from Italy. So, how could you not leave satisfied.
Manny’s – Manny’s Cafeteria and Delicatessen has been around since 1942…. With that amount of time in the industry they must being getting something right! If you are looking for something simple and delicious this is it!
The Berghoff – Here is another restaurant with a lot of history. They have been in the business for 110 years and 4 generations of family ownership. Here is a place that you don’t want to miss! Come on in and get some great food.
Gene & Georgetti – Gene and Georgetti is Chicago’s oldest and one of its finest steakhouses. So, if you are looking for a great steak come on in and give Gene and Georgetti’s a try!
Gibson’s – Gibson’s has a few locations, one of which is in Chicago. Here is a great place to grab a steak! You won’t regret stopping by.
Yoshi’s Café – Here you will find great food and a comfortable atmosphere. The food here has its own unique twist to it, leaving you wanting to come back again and again.
Pump Room –The Pump room offers you a number of things. These things include reasonably priced “favorites” and a comfortable environment with which to enjoy them in.
Arun’s – Arun’s is a top notch Thai Restaurant! You will be taken away to the exotic lands of the Thais. You will not only have amazing food, but dine in a beautiful environment!
Everest – Breathtaking views are one of this restaurants great qualities. This restaurant is located on the 40^th floor of the Chicago Stock Exchange. Bronze sculptures really make this place shine. You won’t regret eating here!
Café Ba Ba ReeBa – Chicago’s Original Tapas Bar! There is a ton of great food here, so make sure you bring your next date here!
O’Brions – Here’s a classic restaurant/bar that is found in Chicago’s historic Old Town Neighborhood. Come on in and enjoy a juicy steak or a delicious Angus burger. You won’t regret it!
Carlos’ – Carlos’ recently celebrated 30 wonderful years! With that kind of experience you can’t go wrong with this contemporary French cuisine.
Mortons – Mortons is “the steakhouse”! If a steak is what you are craving, then look no further. You won’t regret eating here.
Brazzaz – Get your Brazilian fix by eating at this Brazilian steakhouse! Here you will get a unique dining experience that you won’t find at many other restaurants.

Best Bars/Lounges in Chicago

Here is another common date idea! The common phrase is “let me buy you a drink”, which has been very successful for getting dates for a long time. This is a tried and true date idea, but in Chicago there are a number of bars and picking the perfect one for your next date could be difficult. Some bars are a little more casual, some a little more upscale and some have more of a party atmosphere. All of the bars listed below are top-notch and will provide you with plenty of variety! Browse and enjoy.

Photo via Rice-Aron Library

Telegraph – Telegraph provides you with a comfortable atmosphere like no other! Here you can enjoy some wine from the wine bar or grab a little something to eat while lounging with friends.
Roof – Be above it all at this wonderful bar/lounge! You will be sure to have a unique experience if you choose to stop on in here.
Leadway Bar – Beer? Wine? Mixed drink? No matter your poison Leadway has you covered. Come on in with your next date and have an environment to cater to your personal experience.
EnClave –Looking for a little bit more of a party atmosphere when it comes to your bar? Then look no further. EnClave is a bar, but also a venue. You will be sure to be entertained.
Maria’s – Maria’s packaged goods and community bar is a place to come for great drink, food and the company of others.
Sound Bar – Here is a place to party and have a good time. Sound bar gives you a great atmosphere guaranteed to give you a great time!
The Underground – Located in Chicago’s River North neighborhood, The Underground gives you an environment you won’t find anywhere else. Here you can find international DJ’s, celebrities, and a cutting edge nightclub!
Vision – Vision has received many great awards such as being voted #1 Mega Club in the US by URB Magazine and top 100 clubs in the world by DJ Mag. Vision is definitely a night club you don’t want to miss.
Bin 36 – Wine, wine, and more wine! Bin 36 has everything wine related that you need. So, if you want to get something to drink, but show a little class this is your place.
The Gage – Here is a tavern like no other… Grab a bite to eat with your drink. Gage provides you with vintage décor that helps give you a comfortable environment to relax in.
Nacional 27 – Eat, drink, dance, party and be merry! If you’re looking to show your upcoming date a great time this is your place.
Cal’s Bar – Cal’s is a great place to relax and have a drink or two… or more. If you are looking for somewhere casual to take your next date this is it!
Potter’s Lounge – A new twist on legendary cocktailing! What else could you ask for in your lounge? Nothing! Become a legend at Potter’s lounge.
Angels and Kings – Angels and Kings will make you feel like you are royalty! Here you can get a great atmosphere that will make you feel you are in a place above the rest.
Crimson – This lounge is has a feel that is vintage, but gives off a unique spin. You will be sure to be impressed with the environment with which you are drinking in as well as the quality drinks you can get here.
Muraski – Murasaki Sake Lounge gives you great sake as well as other spirits and cocktails. Come on in and have a drink and maybe do a little karaoke!
Pops for Champagne – Here is a place with a little more class! Pops is one the nations most acclaimed champagne bars, so it should come as no surprise that is is also one of Chicago’s finest night clubs. You can’t go wrong here!
Old Town Social – 23 large format and projection screens are what you will find here! You will always have something to watch as you enjoy your beverage.
Delilah’s – Delilah’s gives you great selection of beer and liquor! Will be sure to get what you are looking for. So, come on by!
The Galway Arms – Voted “Best Irish Pub” in 2010 by City’s Best Chicago! Galway’s is a classic Irish Pub where you can watch all of your upcoming games!
Webster’s – Here is a bar, but of a different kind… Webster’s is a wine bar. So, if you aren’t a beer or mixed drink person, or even just want a different atmosphere Webster’s is your place.
Jack’s – Jack’s Bar and Grill is your neighborhood watering hole. Jack’s can be found in the Lakeview neighborhood and provides you with both great food and drink.
Duke of Perth – Here’s a classic Scottish Pub! So, if you are looking for an atmosphere that is comfortable and friendly, and food and drink that will leave you satisfied this place is for you.
The Long Room – You, us, beer, and a room! That is what you will get here. To some that may not sound like much, but it is more than a wonderful experience.
MiniBar – This ultra lounge and cafe provides you with might drinks, mighty eats, and might party! So, make your reservation and come on in today.
Scarlet – The theme of the Scarlet Bar is that of the 1920’s. So if you are looking for something a little bit different and unique, but with a touch of class this place is for you.
The Bar on Buena – The Bar on Buena has been dubbed the Best Pub Grub and I would have to agree! This place is a definite must if you are in Chicago.
The Village Tap – Here is “Chicago’s Draft House and Best Beer Garden”! If you’ve never been to a beer garden this is a great one to go to!

Best Comedy Clubs in Chicago

Comedy equals laughter and laughter equals a good time! So, it would make sense that if you are wanting to have a good time on your next date that you should go where the laughter is…. what is a better place to find laughter than a comedy club?! Chicago has numerous comedy clubs, so we have helped to narrow down the list. You will be sure to have a great night if you stop on in for a comedy show at one of the comedy clubs listed below. Browse and enjoy.

Photo via Bruno Lestrade

The Second City – Whether you want to learn on to be a comedian yourself or whether you just want to have someone else make you laugh this place is for you!
Zanies – Zanies has been dishing out the laughter for 33 years! So, they must know how to get a good laugh. You won’t regret coming here.
iO Theater – Here is “Chicago’s Best Improv Theater”! If you want a good laugh that you won’t see coming (and the comedians won’t either!), this is your place.
The Comedy Sportz Show – If you like sports and you like comedy then this is your place! Here you will get team vs team comedy. See whether you think the red or blue team is funnier.
Chemically Imbalanced Comedy – Here you can find all things comedy. So, if you want to impress your date with some great comedy stop on by.
The Annoyance Theatre – The Annoyance Theatre has you covered in all areas of comedy whether you are looking for a show, to take a comedy class or host your own private event they’ve got you covered.
Jokes and Notes – This place provides you with a place to unwind and relax. You will be sure to have a good time here if you bring your next date here.
Chicago Underground Comedy – This comedy club was labeled by Chicago Magazine as “The Hippest, Hottest Stand-up Showcase to emerge in years”.

Best Sweet Shops/Bakeries in Chicago

Everyone knows the best way to end a date is with something sweet. Have the right dessert can make the end of your date the best that it can be. Chicago has a number of places to grab something delicious, so we’ve helped you out and narrowed it down to the top ones. Check out our list so that you can make sure you next date ends the best way it can. Browse and enjoy.

Photo via Fripy/Lau

Zelda’s – This sweet shop has all of the delicious creations you could hope for! Bringing your next date here would be a sweet and delicious occasion.
Sprinkles – Want some delicious and fresh cupcakes? Well, look no further. From the moment you walk in the door your mouth will be watering.
Sukhadia – Want an interesting twist to your sweets?! Well, check out this Indian sweet shop. You will have a unique and delicious experience!
Roeser’s – A tradition of excellence is what you will get here! Delicious cakes, cookies and more are what you will find here.
Alliance – Alliance Bakery is a place that’s specialty is cakes! If you are looking for a place to get your next custom cake done then look no further, Alliance has you covered.
Dinkel’s – Here is a bakery with four generations of history! With Dinkel’s history in the business you are sure to get something tasty here.
Corner Bakery Cafe – This bakery provides you with the sweets your are wanting…. but they also provide you with a little bit more. You can come on in and enjoy one of their delicious sandwich’s or one of their other entree’s.
Sugar Bliss – This cake boutique is here to provide you with some truly delicious eats. Your cake will not only taste amazing, but look amazing as well!
Pleasant House – Pleasant House has won a number of awards such as “Outstanding Restaurant 2012”, “Best Cheap Eatery and Farm to Table Restaurant”, and “Great Neighborhood Restaurant 2012”. With those type of awards you can’t go wrong here.
The Bleeding Heart – Bleeding Heart Bakery is here to give you a bakery, with a twist. This “Punk Rock” bakery will give you a new, unique idea of what a bakery can be like.

Helpful Chicago Blogs

Chicago is a huge city with a huge diversity of resources and opportunities. This can seem overwhelming. How can someone be expected to find the perfect restaurant, club, museum, etc? Luckily the advent of blogs in the 21st century allows us to sample the expertise of Chicago’s most knowledgeable residents on practically any subject, and at our leisure.

Photo by Baddog_

Singles Mingle– Mingle Around is boutique matchmaking firm and singles event company based out of Chicago, IL. The blog features dating advice from the matchmaker, Jill Jackson, as well as dating horror stories, great date ideas and flirting tips.
Jeff Eats Chicago– Jeff’s blog packs a lot of valuable details and photography on hundreds of restaurants into a very small space, making him one of the most useful and highly regarded food blogs based on the Windy City.
EdgeVille Buzz– Get the latest scoop on whats happening in Chicago’s diverse Edgewater and vibrant Andersonville neighborhoods. EVB features restaurant reviews, a calendar of events and coverage of arts and entertainment in the area.
Fine– For in-depth reviews of Chicago hotspots, and photography that is nothing short of spellbinding, take a visit to the Fine, Design, Dine & Wine Blog.
Cheeky Chicago– Cheeky is an online magazine exclusively for cosmopolitan women. Featuring dining, nightlife, arts and culture, beauty and fashion, health, fitness and relationships, Cheeky is the newest what-to-do and where-to-go guide! Plus, with the Cheeky Card, readers can get VIP experiences at the hottest spots in Chicago. Being confident enough to treat all women with respect–that’s Cheeky!.

*If you would like to be added to one of our list above please email luke@datingwebsites.com