You may not have booked your ticket to Chicago just yet. But, just in case you do, we’d like to return the favor (and tempt you just that little bit) – by taking you on a whirlwind trip around the more individual sights of this so-called windy city.
Day One
We suggest you base yourselves at the boutique-like James Hotel in River North – a former warehouse district famed for its unique shops, art galleries and trendy bars and restaurants. It’s perfectly positioned near – as well as far enough away from – downtown Loop’s more touristic hotspots (The Reliance Building, Chicago Theatre, Civic Opera House and Buckingham Fountain included).
The Loop’s a great place to get your bearings, though, and whilst there you might as well stop for brunch at celebrity chef, Stephanie Izard’s outlet, Girl & The Goat on Randolph Street. The interior’s impressive in itself but the huge varieties of small-plates are what keep punters coming back. From here you can walk off your feast with a wander down to Lake Michigan and around the Chicago harbor area.
Pop in to the Swisshotel to rest your legs, grab a drink and a snack (their cheese and chocolate fondues are particularly pleasing) and marvel at the sites from a rooftop vantage. Make sure you stay put on a Wednesday or Saturday evening – it’s one of the best spots for summer-time fireworks displays from Navy Pier.
The architectural cruise on Chicago River is another pleasant way to take in the larger attractions. That’ll drop you back near River North – just walk up Michigan Avenue. Or you can stroll back to your abode and refresh yourselves ready for a night downtown.
Dinner has to be had at the Purple Pig. A collaboration between four of Chicago’s top restaurant players, this rustic and Mediterranean-style eatery offers relaxed dining with a communal feel. Make sure you try some of the ‘smears’ (like Whipped Feta with Cucumbers or Pork Neck Bone Gravy with Ricotta). North River offers a vibrant nightlife but we recommend saving the best ‘til last – winding your way up to Double A Mercadito for late-night cocktails. Trust.
Day Two
Your second day in America’s Second City can be spent living it like a local – with the independent food and fashion outlets around Logan Square.
Start at Longman & Eagle for brunch where greasy hangover cures are plentiful – cheese grits, fried chicken and waffles or their signature beef fat fries are famous at this joint.
Then move on to the shops – Wolfbait & B-Girls for cool locally designed accessories, Freak Boutique in Bucktown for the cheap and cheerful or Reckless Records for the music-lovers among you.
Big Star is great for a quick refueling – Chicago has one of the biggest Mexican communities outside of Mexico, so tacos are top notch. The outdoor patio is great for people watching too.
Your last evening should be spent at the Loop’s Chicago Theatre. From the city that brought us modern improvisation and classic musicals like Chicago and Blues Brothers, there’s sure to be something to suit each of your tastes. Regardless, the theatre’s own grandeur is enough to leave you breathless. With gilt gold, sweeping staircase and mural-covered ceiling, it’s true 1920’s elegance with an added touch of French Baroque.
Handmade al fresco cocktails can be had year round at the stunning Roof at The Wit Hotel (each table comes with its own warming fire pit). Or take a taxi to Lincoln Park’s romantic North Pond restaurant. Its setting overlooking the pond with the city skyline as your backdrop makes it one of the best places to wind down and recount your whirlwind trip around the windy city.
