there's so many, many things to do in chicago - restaurants, navy pier, millennium park, bars, zoos, museums, even mini-golf. yet there's so many nights where we're debating what to do or even where to eat for dinner. sometimes having 400 options makes it hard to pick just one. so i complied my favorite go-to date night ideas. sure, i love going to the shedd aquarium, watching live bands, or seeing a bears/cubs/blackhawks game, but i'm talking about my favorite ideas for what to do when you're just thinking last minute 'what are we doing tonight?!'
my personal favorite date idea is definitely wine tasting (or beer tasting.) chicago now has a winery right downtown. it's near my place, in the west loop. city winery has tastings and tours, and it also has a full restaurant for a complete date night. you can even make your own wine, with custom labels! it's a pretty fun place. there's also a lot of wine bars/restaurants scattered around chicago, so you're sure to find one no matter what neighborhood you're in.
stand up comedy is something chicago is well-known for. it's the birthplace of second city, which has had so many famous people come from there i couldn't even list them all, from belushi to fey to wolfe. second city is a fantastic date night. they have the main stage shows as well as shows on the smaller stages if you're on a budget/out of planning time - they are just as hilarious and likely to have last minute tickets available. since second city is in the heart of old town, they also offer dinner and show packages with a lot of nearby restaurants. personally, i just eat downstairs (literally, right under the place) at adobo grill. and by eat, i mean drink margaritas and scarf down inhuman amounts of their made-table-side guacamole. like wine tasting, second city isn't the only improv game in town so you're sure to find more options near you.
you can also bring out your competitive side. downtown chicago has a dave & busters. this shocks city dwellers as much as it does out-of-towners. but yes, it exists! i've made john take me there, it's a lot of fun to get competitive and act like a kid again. i dominated him in air hockey. there's also sluggers, in wrigleyville, which has indoor batting cages and carnival type games like skee ball. you can even try your hand at bowling at 10 pin, which i hear is a celebrity favorite (i've never seen one there though.)
drinks with a view is a great quick date option, if you're not planning on a whole dinner. there's so many places with great skyline views and though the martinis at the signature lounge on the 96th floor of the john hancock building will run you upwards of $12, the price is worth it. i also recommend the terrace at trump tower (if you go on a wednesday/saturday during the summer, you see fireworks at eye level) and the shanghai terrace at the penninsula hotel. obviously these places serve food as well - but it's expensive. best to have just a cocktail or two, and maybe an appetizer. the view is something that shouldn't be missed.
restaurants with a (different) view is a great option for an extended date (and you can find places with cheaper options than where you'd go just for a few fancy drinks). i mean, the whole city is also on water. well not on it, but you know what i mean. the restaurants that border the lake are limitless and there's also new options constantly popping up along the river, which winds right through the loop. (i practically live at south branch during the summer.) you can even take water taxis to get to them if you wanted! there's a lot of fancy options, but my favorite has to be bridge house tavern - because you can add bacon to anything on the menu for $2. if that's not a reason to love a place, i don't know what is. and for a completely casual option, try lizzie mcneill's, an irish pub right on river before it heads out into the lake. it's perfect for summer because you can enjoy all the outdoor seating with your pup. well, hawkeye enjoys it at least. she gets a hot dog.
what are your favorite date night ideas?