Chicago gets its whole own post here because we head down at least 2 – 3 times annually. We don’t always stay downtown since we have family in the ‘burbs and can take the commuter train downtown for the day, but we have stayed downtown a lot, and it truly feels like our second home.
Getting there: We always fly in to O’Hare because we usually fly Air Canada or on points. And when we have a spare 10 hours (each way!), we’ll drive from TO.
Where we’ve stayed: We usually stay in the Loop or close to Michigan Ave – here are a few of the places we’ve stayed:
Magnificent Mile/River North hotels
- The James Hotel: Hands down, our favourite in Chicago – we’ve stayed multiple times and nothing has compared. Close to everything, free wifi, free upgrades sometimes, super chic rooms, great gym, great spa (with reasonably priced massages), will accommodate an early check in and regular check out is 2 pm, great products, beyond friendly staff, and for the Chicago marathon, a special early morning continental breakfast and coffee for runners. No bads at this hotel.
- Omni Suites: Nondescript suite hotel, free wifi, big bedroom and front room, decent gym, friendly staff.
- Sheraton Hotel: Giant hotel, good meeting spaces, room overlooking river was great, trusty Sheraton, but nothing really stands out about our stay.
Loop (and Loop-ish) hotels
- W City Center: The latest hotel we just stayed in – it’s the usual W clubby vibe, but a little less so than others we’ve stayed at. Free wifi in lobby but $15 in rooms, free coffee and hot chocolate in the lobby in the mornings, too. Room was smallish, but comfy, and sometimes we could hear our neighbours talking. Very friendly staff and great location close to Union Station and the subway/L-train. Make sure you ask for a courtyard-facing room here so you don’t hear the L when it goes by. Although we didn’t use the gym, it’s small but well equipped. There also seem to be good deals at this hotel because it’s a bit off the beaten path as far as hotels downtown are concerned.
- Hotel Burnham: A lovely Kimpton hotel in an old building, typical over the top Kimpton styling, but comfy overall, good products, no gym (at the time you could get free passes to a nearby fitness centre – I chose to run along the lakeshore instead).
- theWit Hotel: This is a Doubletree hotel – but don’t let that deter you – it’s a great boutique feeling hotel. We visited when it was recently opened, and unfortunately dpr was sick the entire time we stayed (note: the bathroom floor is do-able for a bed…TMI?!). You get a warm cookie on check in! They charge for wifi – so cheesy, but the gym is also good. There is a roof top venue that we missed, and one downside is that it’s right next to the L, so if the sound of the train going by all day/night is going to bother you, this could be an issue, or you could just ask for something far from the L.
- Chicago Crowne Plaza Metro Downtown: This was an excellent, well priced hotel, just outside of the Loop, but within easy walking/taxi/transit distance of the Loop. We stayed here for a family member’s wedding, so got a good, prearranged room rate. Rooms were updated generally (bathrooms were a bit dated) and a good size, with a nice balcony (no furniture, but nice to have the space). Parking was a bit crazy, but there’s a number of pay lots nearby, there’s wifi, and the gym was updated and well equipped. The area is interesting, and up and coming, and there is a grocery store across the street and lots of restaurants nearby. For a budget choice with a downtown location, this is a good spot.
Fun: So much to do here. Not sure we’d call it fun, but dpr ran the Chicago marathon in 2011. That’s probably enough for awhile, but running along the lakeshore is always nice. If art is your deal, there’s a great art institute here (watch – it usually has a free evening once a week), there’s also a museum of natural history, aquarium, IMAX, etc. There are all kinds of boat tours of architecture and the lakefront, and walking tours, too. There are lots of neighbourhoods to explore – besides downtown for shopping (Michigan Ave, the Gold Coast, and shops in the Loop) we try to get to Bucktown or Lincoln Park, and Wrigleyville is also a nice neighbourhood. Lots of great food, too – we’re always on the hunt for red velvet cupcakes or cake and Sprinkles (a cupcake vending machine!) and the Goddess and the Grocer deliver. Epic Burger serves a wonderful organic/hormone free patty and yummy fries. We also love to hit up Nordstrom Rack (there are 2 downtown), Room and Board, Aveda (why are the prices so much cheaper here than in Canada??!!), and Barney’s. There’s also Millenium Park for a lovely stroll. And back in the day, we could get Blackhawks tickets, but now not so much.
Tips: 1. It’s super easy to get around the public transportation system here. You can buy a day pass and ride all you want for about $5. You can even get from both airports downtown on the subway. 2. People here are stupidly friendly – if you ever have any issues navigating, don’t be afraid to ask. 3. The Metra train is also an affordable option if you’re staying outside of the city vs. driving in/dealing with traffic/kissing at least $30 goodbye for parking. 4. Check out the freebies for the museums/other sites during the week – there’s usually a few hours one night where you can get in for free. 5. Watch for super busy times in the season – hotels downtown can actually sell out altogether on the marathon weekend, or when big conventions are in the city.