The motto here is, "We were tiki before it was cool," and it certainly rings true from the moment you walk into the doors to this massive, yet somehow intimate, tiki bar, just on the outskirts of the city. There's not a hipster in sight, just very boozy tiki drinks in a setting that takes you farther away from Chicago than the River Grove location actually is. Open since 1964, the enormous space is met with an equally giant cocktail list, boasting well over 100 drinks concocted with any combination of booze you can imagine. Since the overwhelming menu isn't for the faint of heart, try ordering a tiki flight to sample your way through the list. Semi-regular Hula shows take place at Hala Kahiki, and it's the only night the bar serves up more than a bowl of pretzels with its tropical drinks. Instead, guests can enjoy a full Hawaiian dinner with the show. Pop into the attached gift shop before heading home to take a bit of the tiki kitsch home with you. —Erin Delahanty
Lettuce Entertain You's tiki bar appeals to its River North clientele expertly. The entrance to the bar is in an alleyway and you walk down a long set of dimly lit stairs lined with skulls to get in—but once you're there, the dark oasis is filled with tiki decor and drinks that are boozy as hell. Beverage director Julian Cox fills the menu with tiki standbys and new takes on drinks that are all guided by your taste on the menu. Looking for something refreshing? Grab the Surf Report, with foam and in a surf-shaped mug. Want a classic? Go for the Three Dots and a Dash, in a tall skull wall glass (our favorite). Groups should grab a large-format cocktail like the Zombie, a fruity and spice–filled punch bowl with a fiery garnish.
On most evenings, Ward Eight is a typical cocktail bar (a very good typical cocktail bar). But on Tuesdays, the bar turns into a tiki paradise, with a totally different menu, which is encouraged by all the bartenders to anyone who happens to stumble in unaware of their new tiki surroundings. For those who want their tiki light, this is a great introduction to rums and agricoles. Grab a rum old-fashioned to try something familiar or grab our favorite, the Queen's Park swizzle, to enjoy the evening at this Evanston bar.
It’s hard to re-create the magical paradise of Hawaii in a strip mall in Des Plaines, but Tiki Terrace gives it a valiant effort. From the thatched-roof tiki bar to the enormous Easter Island statue heads scattered throughout the space, the island theme of this kitschy spot is hard to escape. Come during the week or for a weekend lunch if you’re dying for a Spam burger—you won’t find it on the Friday- or Saturday-night menus, when guests pay $21 for a cheesy, hula-heavy island-themed show and one of a preselected group of entrées (fried coconut chicken, fried mahi mahi). Skip the fried stuff and opt for the kalua pig with a side of taro chips and a delicious tropical cocktail. The drink—combined with your tempered cynicism—will allow you to appreciate the Terrace as a fun birthday spot or staycation escape.