Dating in Chicago is galvanizing to say the least. The windy city offers so much for singles and has some great dating spots you can hang out at to take your relationship to the next level. If you are still struggling with converting your first date into subsequent dates, here are 12 dating tips to single Chicagoans which will help you get successful in your dating endeavours:

dating in chicago

1. Do not make your date choose between their love for you and love for food.

Chicagoans love their food and if you make them choose between their hotdog and you, chances are that you will end up single again as this city loves its hot dogs. Take them to their favourite hot dog stand and see how this date magically turns into one of the most successful dates of your life. The city also has many Michelin-starred restaurants so you can go to one of those if you want a fine dining experience.

2. Cozy up with your date in a romantic café during winters.

Chicago has a bad reputation for its chilly winters but this can be the perfect time for you and your date to snuggle up to each other at home or at an outside café which offers bonfires and hot coffees. Chicagoans love their winters and staying at home with your partner will only spice up the things further.

3. Take them down to the lake for some quality time together.

Summer season in Chicago is one endless party but if you both want to spend some quality time alone, head down to the lake or to the Riverwalk area to check out the new cafes or for simply taking a walk together. You can take a leisurely stroll and enjoy the food pop-ups along the lake also. Chicago has many craft breweries which can be visited if you want to sample some locally made beers with your date.

4. Show true love and respect for their family.

Chicagoans love the city and many generations of one family can be found living in the same city. It is very important that you show interest in your date’s family and interact with them also to score some brownie points. Respect your date’s grandma and you will surely be asked to stay for dinner.

5. Offer to take them back to your place for a coffee.

Most singles in Chicago have their own place to stay since the cost of living in the city is affordable. This eliminates pesky roommate issues so you can invite your date in for a cup of coffee and take things forward from there if you both find each other interesting. Chicagoans are generally great at being frank and funny so there is nothing you would not like.

6. Do not date someone with different sports preferences as you.

This city takes its sports seriously and legit breakups have happened when the favourite teams did not match. Whether you are a Cubs or a Sox fan, make sure that your date is on the same page as you otherwise it will only lead to screaming matches during the games and your dates would be ruined. Having the same favourite team also means that you will have a great time during matches and have someone to rejoice with if your team wins.

7. Work for getting Lollapalooza passes arranged for them.

Chicago residents do not like missing the biggest music festival their city hosts and they will only get angry if you turn up without passes. Make efforts to arrange for the passes for this music festival to impress your date and increase your chances. Chicago also hosts some other music festivals but the Lollapalooza is the one festival you should not miss.

8. Do not plan an outing when the football season is on.

There is no point going out when the football season is on as everybody who is living in Chicago loves watching football and prefers to stay indoors or attend the match. If you can get the tickets for a football match then nothing better but if you can’t, make plans to stay indoors and enjoy the match.

9. Be upfront with them about your intentions.

There is nothing that singles in Chicago hate more than a person who is not upfront about his or her intentions. People here are very sweet and talk straight about their preferences. They also do not have any problem with sleeping together on the first date so if you are up for it and your date it ok with it, why not have some fun on the first date itself.

10. Get a couple selfie at The Art Institute.

Dating a single Chicagoan means that you can get entry into the legendary Art Institute easily. This museum has been termed as the best art museum in the world by TripAdvisor so it can be a great date if you both love arts and culture. From Van Gogh to the Duchamps, this museum offers something that cannot be experienced anywhere else in the world.

11. Profess your love for Chicago as much you can.

If you love this city, be vocal about it. Chicago residents take pride in their city and they will love hearing it from you too. Professing your love for this wonderful city will only get you closer to your partner and will make them treat you like one of their own. Since the city gives you so much, it is an easy task to love it.

12. Do not make them travel alone from Logan Square to Loop.

Accompany your partner when travelling on the L route to protect them from weird people hanging out on the route. Not only with you spend more time with your partner but you will also make them feel safer and protected. Chicagoans do not expect you to pick up and drop them home but this is a nice way of telling them that you care.