Top 5 Date Night ideas in or around Chicago, IL
  • Mari

Top 5 Date Night ideas in or around Chicago, IL

Hello Again!

Thank you for tuning back into Simply Amari, I hope everyone has had a great week so far!

How is it that whenever you need to do something or have to plan an outing you can never figure out what to do?

This weekend is Jay’s 23rd birthday and I am in charge of planning what we should do and for the last couple of weeks I have come up with nothing. Okay, I shouldn’t say anything because in reality I came up with a ton of options but either he has turned them down or they just haven’t been in budget. I love him don’t get me wrong but both him and I are not the type to make our birthday a big deal, usually we just go to dinner and have a night in. This year I wanted to do something special for him because he has been working really hard and to be completely honest our relationship has been on rocky ground and we are trying to get our groove back. So I wanted to make this birthday extra special for him to show my appreciation and just show him how much I love him.

I have been searching far and wide for some fun activates to do but every time you put in “things to do in Chicago” nearly all of the search results are for kids or bars. Both are things we don’t want to do for his birthday, especially since Aria will be having a slumber party at grandma’s house. Plus, Jay and I are not big drinkers and when we go out and drink its maybe 1 or 2 drinks so spending his birthday at a Bar just wouldn’t be fun for us.

After searching and coming up with pro’s and con’s for his birthday, (which is on Sunday August 11th) I finally narrowed it down to 3 places but I still can’t figure out the top place so what I am planning is to have him pick a number 1,2,or 3 and we will do whatever number he picks. With that being said though I did create a long list of things to do in Chicago that are super fun and were top contenders for birthday’s, anniversary’s, or just plain date nights.

Here is my list of Date Night places to go in (around) Chicago:

K1 Speed

For those of you who don’t know what K1 Speed is, its an indoor go-cart arena. They have locations all over the US and there is two locations in Illinois, one in Addison and one in Buffalo Grove. Personally I have only been to the Addison location but there is 2 tracks and a full lounge restaurant and two bars. I actually have a ton of fun going to this track because the electric go-karts go pretty fast, like 45- miles an hour fast and they make it really safe. Pricing wise its actually not to bad, and they have great deals so you can spend the whole day racing,

Like for 2 races a t-shirt and the membership its 55$ a person, (the membership comes with loads of discounts and little perks that you can find here: or if you just want the races they have a varaity of prices per race ranging from 22$ -50$.

For those of you who don’t know Jay is a huge car guy and loves to race which usually scares the booboo out me but I don’t mind going here because its pretty safe and I am able to join in on the fun and we make competitions up as we go.


If you are a thrill seeking like me iFly is probably one of the most fun places to go for a date night. I think this also preps you for doing the real thing if you are up for it! So what is iFly? Glad you asked. iFly is an indoor skydiving arena, yup skydiving. Its all the fun of flying without the plane. There are locations all over the Chicago Area from downtown to Rosemont and Naperville, and with awesome instructors that walk you through the whole “flying” process and make sure you are in a controlled, safe environment. They do have multiple packages based on your flying skill and whether or not you’ve been there before.

If you are a first time flyer like us, they have multiple packages including these two packages, the Takeoff Experience and the Airborne Experience, which include multiple flights per person, gear rental and training. The prices range from 59.95-279.95$ which you can find more information about at their website over at:

3. Wrigley Rooftops

If you are from Chicago this is probably one of your favorite places to go, its definitely mine. Wrigley Rooftops are so much fun and as a long time Cubs fan, yes before they got cool, I always loved going to the games and just have a night or day on the field. The Rooftops are completely different though, not only do you get the game but endless drinks, food and beer it’s a fan favorite. I actually was planning this to be what we did for his birthday but the Cubs were playing in Ohio on his birthday so that made it a little difficult to go to the Rooftops. Plus, Jay being from California he’s not a big Cubs fan or Baseball fan in general so while I would have been loving it, he would have just been happy being with me. The prices range between 131$- 199$ (based on game and what building you want). In my oh so humble opinion this is great to spend the whole day at the game since you can arrive hours before the game starts and start drinking and really getting the maximum out of the day.

If you want to check out prices or see game dates be sure to check out this website:

4. Lake Cruises

This is probably more for me than for him, Lake Michigan has these awesome boat tour/ dinner options. There are a few different ones, like the Odyssey Chicago Cruise, Spirit of Chicago Cruise and the Mystic Blue Cruise. Each one of these has different eating options that you can pick from, either brunch, lunch, dinner or late dinner, during the summer they even have Firework Dinner Cruises. Taking a cruise around Chicago is a lot of fun and really romantic to be completely honest meaning it also comes with a nice price tag. The prices vary from boat to boat and then what time you go to eat and tons of other variables, which you can find on any of their sites, ( ). So what do you get? While the amount varies for the most part you get the cruise at whatever time you choose, then dinner. At all of the boats I looked the price includes the dinner too, some packages include an open bar while others don’t. I was trying to decide if this was going to be fun for Jay or romantic for me, which in all honesty he would have been happy to spend time with me but it’s a little to girly for his speed.

I highly recommend this option for a romantic date night its worth the extra money to spend time with your other half on a romantic cruise.

5. Sycamore Speedway

This one is perfect for us ladies who never know where to take the men. Sycamore Speedway is a race track in Maple Park, IL, they have tons of different races from Old School night to Sizzlers and Bubble Gum Races. Jay absolutely loves cars and races so this was by far the best option for us to do his birthday if it wasn’t for the stormy forecast this weekend. They usually have their races all weekend from Friday- Sunday the pricing is also not that bad, on a regular race night its between 5$ for kids 12$ for adults. On special event night the price does go up but not by much. I am not a car girl or even like races in the slightest but I even have fun going to the races there is a lot to do and its just a nice place to get a little dirty.

Leave the heels at home and opt for boots or gym-shoes, it gets a little muddy.

To be completely honest with everyone as I was writing this I pretty much picked what we will be doing for his birthday, I guess writing them down and talking about them out loud really did help. I want to keep where we go a secret since he hates surprises as much as I do. I hope at least someone found one of these options to work for them and help find a quick date night in the area.

I will also make a list of date nights for under 50$ since I love to save money and be on budget!

If you know of any other places that would be fun and worth a drive for a date night leave them below!

Thank you always!

Amari R


©2019 by Simply Amari. Proudly created with