So many times I have started writing a travelogue on Chicago, after all it’s only natural. It has been my favorite vacation, hide-out and go-to spot for so many occasions, so many people and so many reasons. In the last few years among a million moves, this is one place I have ‘visited’ every year at least once, in some years in every season, in this year, I stayed back for a whole season. Southwest airlines gave me 3 free roundtrips to Vegas, I flew so much to and from Chicago.
And that many times I have backed out and fled the challenge (of writing the travelogue) because every visit to this city, I opened a new page, discovered a new sculpture, a new favorite food, a new neighborhood!
Living in a place, growing a habit, having a fixed bed to sleep in and a vehicle at your disposal often rots the well-honed tentacles that guide you in the land of new and unknown.
And this summer in Chicago is making me lose my edge. So before it’s all gone, while I keep looking for and rediscovering Chi-town’s chic-ness, I’d like to pen down a few brief pointers, things that came in handy for me when I was a tourist.
Always fly into Midway rather than O’Hare, you will save an average of 45 minutes each time you choose the former over the latter, plus Midway has a Potbelly Sandwich store and has Southwest flying into it. 😉
Always walk, don’t drive. If you are a shopper, a foodie, a photographer, an adventurist, a people-watcher, or a thrifty combination of all above, please walk and use the CTA. Parking like in most big cities is expensive and rare and tough. If you have a license plate from anywhere other than IL, you are on the special menu for the city’s revenue system. But that’s one of those secrets everyone knows, but only few are shameless enough to talk about.
Always book a hotel close to downtown ‘the loop’, or absolutely within walking distance of the El (or Elevated CTA train lines). You might spend in taxi rides and transportation what you save on your hotel stay.
When I was not staying at home, with friends, or family, these are the places I had spent my nights: Intercontinental Hotel Rosemont (near O’ Hare), La Quinta Inns and Suites (near O’Hare) and Rodeway Inn on Ogden Ave. Intercontinental was one of my best hotel stays ever across the globe, that kind of service, décor (that’s important for me), stay is a steal for only $150, now that I think, it could have been on a special. LQ was a good value for money, but not the greatest service: I’ve stayed at better LQs and the Rodeway Inn I guess I didn’t know any better, a dismal 2.5/5 for value was a great learning experience.
Friends and family who have hosted me on other occasions were all well located: Hyde Park (accessible by the Metra and #6), Forest Park (..by the Green line and Metra), downtown on Madison (by everything!)
Next the touristy spots: you will probably want to do an observation deck? Choose the 4th tallest in the city John Hancock over the tallest Sears er. Willis tower. Why? Well Big John offers candid views of blue-green Lake Michigan and better views of all things nice and tall (including Willis) that defines Chicago. It also has history framed in photos and words for a overall good time. Big john has a restaurant high up, which is more famed for the views than the food or value for money; contrary to a bunch of good eating places downstairs, including Jamba Juice and Cheesecake Factory (both of which we love despite being chain-restaurants).
Also while you’re up there, try to go a little before sunset, so you can see the city by day, (maybe some of Indiana too?) a glorious sunset and the city-lights when dark.
If you’re like me, you like cheesy. Navy Pier might just be the funnel-cake smelling, souvenir selling, junk-shopping, street-food eating respite from the walk. It has something for every one. A Beer Garden, a Stained Glass museum (showing Mosaics too currently), a Children’s museum, a make-a-bear store, Bubba Gump Shrimp, American Hot Dogs, Ben and Jerry’s and fun stuff from across the globe in a vendor market type atmosphere. Unwind, relax, catch some magic show for kids or watch the fireworks if you’re lucky 9pm Wednesday 10:15pm Saturday in summer (subject to change), also July 4th 9:00 pm and Dec 31st midnight.
You’d probably like to take a boat-ride along the plentiful water of the lake. There are many companies, Wendella, Seadog, Lakeshore, Chicago Architecture Foundation, Spirit, Mercury, Caravan…. to name a few. Which sounds the most authentic? Chicago Architecture Foundation. Wrong choice, unless you want a dead-with-boredom, grumpy, drone-y explain Chicago’s magnificent architectural wonders in a pin-point fashion.
I have taken about 6 different boat rides, some many times and I can see why you’d prefer SeaDog’s speed boat tour, or Wendella’s 90 minute lake and river or Tall Ship Windy for obviously thrill, : best value (fun, info, relaxation) for money and some good time sailing with a special someone. Fancy watching the fireworks from afloat the water? You can, just schedule accordingly!
If you’re traveling with kids or love animals and/or are from a place where there are no good zoos or aquariums, you might want to spend a few hours in that niche.
Lincoln Park is free but rather lame. Good for those in the city for a day lazing but not time-crunched tourists. Choose Brookfield Zoo of course for a good tour keep 2.5-3 hours in hand. Go to the Shedd Aquarium, but get tickets in advance. Keep a good 4 hours to include everything.
If you are a art-junkie, try sneaking into the Art Musuem on Michigan, its free Thursday evenings. If you’re a museum addict, you might like the Field Museum. But beware both these will take whole days if you want to do them well, so when planning a day trip you might want to avoid them.
If you have more than a day, definitely spend a day on the museums and check out the individual neighborhoods—their old-style architecture and specially their specialty restaurants. Also educate yourself on the many fairs and festivals of the city during summer and plan your trip accordingly. While traffic and flight deals might be unfavorable, Taste of Chicago or the Blues festival besides many others, are well worth at least half a travel-day.
For an efficient one-day tour start with the sculptures and murals while you have the all the morning energy to walk (or substitute with the zoo and aquarium), take the boat tour, climb up an observation deck, go to Navy Pier and intersperse these with culinary wonders that makes Chicago what it is.
And thus coming to the most important part of any travel: Food.
Chicago has been called a food-lovers paradise so many times and a haven for hot-dogs and pizza. I was not as much a believer in the whole hot-dog works thing or the pizza while I was a visitor and I hang my head low (and high) saying that the last 3 months has done miracles on my hot-dog taste-buds and cultivated special taste receptacles for pizza that I didn’t know existed. And I am not just talking about the quintessential deep-dish pizza, I mean pizza: crispy thin-crust, wood-fired, stone-grilled. Any. All. Now I actually love each one for the specialties that they are.
For Chicago-style deep dish pizza try Giordano’s, Gino’s East or Lou Malnati’s. Everybody has their own favorites that they swear by, I like Giordano’s best.
For thin crust pizzas, Piece (Wicker Park) and Flo & Santo’s (South Loop). Piece’s mashed potato and chicken on white crust happens to be my favorite.
Freddie’s is a typical neighborhood joint with heavy portions sprinkled with Chicago culture. Although known for its double sausage dogs, their tastiest item is their chili
Hot Doug’s is a definite go-to even if you dont do anything else in Chicago. One meal here and you will be coming back to town for more. Never mind the line in front of the restaurant, you will have to wait in line for 40 to 120 minutes and as I have said time and again, it is well worth it.
Doug serves up gourmet hot dogs: everything from the thai chicken with seaweed salad and spicy peanut dressing, to the duck sausage with foie gras truffle, pork with apple and cranberry, the elk, the alligator, the antelope and the vegetarian spinach option among them too…. each getting fancier than the rest. They have specials every day, try those. Duck fat fries (although it doesn’t attract me much) are a Fri and Sat only special. They are strictly cash only and are closed Sundays and most holidays, please check their website and call them for hours.
Another place that catches up on the Chicago dog fever is American Hot Dogs: try each one. My favorite: the Baltimore deep fried dog.
312 Chicago is a hyped downtown joint if you have business to accomplish. Food wise, not recommended at all. Instead walk a few blocks to Grand Lux Cafe on the Magnificient mile and enjoy all they have to offer. My favorite their Creme Brulee duo–the regular vanilla coupled with a chocolate one.
In the mood for Europe? Try Austrian Bakery in the Lincoln Park area. Great sandwiches and breakfast options run parallel to their abundant pastry styles and cakes. Chocolate Croissants and Rum Balls are my favorite.
That brings me to Mindy’s Hot Chocolate in Wicker Park. Take the waiter’s suggestion, because he will say Chocolate #1 which is a warm chocolate souffle with salty peanut butter ice cream served with a pretzel. Dont miss out on the goal. When choosing a hot chocolate try their Black and Tan or Dark French 72%. If you like cinnamon, the Mexican Chocolate might just grab your fancy.
want to bring some for home? Get their cookies, donuts and a hot chocolate mix.
Trust me its all worth it.
More chocolate cravings? Take your pick at hand-made chocolates, gelato and candy at Canady le Chocolatier. He might give you some warm cider to go with your chocolate samples, if you are lucky. Amazing palate cleanser, makes me love his creations even more.
Closeby, for lunch, brunch or dessert and coffee stop by at Little Branch Café for their quiches, lox or dark chocolate gelato or mocha.
Dont miss out on Greektown’s braised lamb (Rodity’s is great, but there are others too like Pegasus, Santorini’s).
Make a trip up north for great Ethiopian family-style food at Abyssinia near Broadway.
Find the many Polish restaurants on Belmont. Try Cafe DK‘s pirogies– the most amazing concoction of meat, cheese and potato.
Russian Tea time near the Art Institute has great breakfast scones and tea.
But dont get me wrong, as much as I love the food scene, I’m drawn to Chicago for my friends and family. People who’d hosted me and helped me settle in, people who’d let me visit at all times of day, those who’ve traveled to visit me while I was here and those who’ve traveled with me. And of course, those who gave tasty instructions of where to try the next greatest food on earth, albeit distantly. And then those, who braved 13F cold and ear-numbing wind, to go chocolate-tasting with me or stood in line for 2 hours in the sun and rain to get hot dogs, walked 10 miles in a day for our famous comprehensive 1 day tour and then dozed off on my knees on the train, or those who’ve driven for hours to catch up with me on airports.
I’m just thankful all these people have great taste!