I'm going to Chicago for a long weekend at the end of this week, and wanted to ask locals what not to miss. Mostly looking for historical neighborhoods, interesting architecture, cultural spots, and outdoor trips (rivers, boat tours, etc) I am somewhat familiar with the city, however don't remember much from my last trip.
Trip Plan Details
- Chicago Architecture Foundation224 South Michigan Avenue, Chicago, IL 60604-2501
- Clarence Buckingham FountainGrant Park, Chicago, IL 60604recommended Clarence Buckingham FountainIn Grand Park! Huge, beautifulRecommended for:
- Pizzeria Uno29 E Ohio St, Chicago, IL 60611recommended Pizzeria UnoA historic and an affordable place to eat. Authentic Chicago Pizza with Italian rootsRecommended for:
recommended Federal Reserve Bank Money MuseumFree admission, take back with you bag of shredded money :) and take a photos with you on $100 bill and with $1 mil. See also how big are $ 1 mill cubes created from diferrent bills. Interesting ... read moreplace. Located 230 S. La Salle St.Recommended for:Local Culture
- Navy Pier600 East Grand Avenue, Chicago, IL 60611-3426
- Ravinia Festival418 Sheridan Rd, Highland Park, IL 60035, United Statesrecommended Ravinia FestivalWhen the weather gets hot in Chicago, Ravinia opens up its doors for concerts in the park. Pack a picnic basket and grab a blanket to spend a night with friends on the lawn (or seats if you pay more ... read morefor the premium seats up front) as you enjoy various concerts each night. Get there early to get a good parking spot and a good spot on the lawn.
- Chicago Botanic Garden1000 Lake Cook Road, Glencoe, IL 60022-1168recommended Chicago Botanic GardenThe Botanic Garden is a great place to spend an afternoon, or even a whole day if you want to relax by the pond with a book. Although the entrance fee is a little steep ($20 per car), you can load up ... read moreyour car with 5 people, making it only $5 per person. The spring and summer are the best times to visit since all the flowers are in bloom. There is also a Japanese area with a traditional Japanese room on display and some more Asian-inspired flowers and trees. In the wintertime, try to catch the Wonderland Express. You need to buy tickets for the Wonderland Express in addition to the per car entrance fee, but it’s well worth it to see many Chicago landmarks intricately made out of acorns, nuts, twigs, etc. and the numerous trains running through the whole thing. There are a couple of greenhouses open too during the winter. If the kids love trains, there’s also a regular train exhibit (separate ticket also required) when the weather is warmer too.Recommended for:Family Travelers
commented on this trip
You might also like walking around the various gallery districts. Pick up a copy of the free Gallery Guide, or check online. I like River North for it's terrific quality galleries, but others are in fun neighborhoods.
- Loyola University Chicago Lake Shore Campus6339 North Sheridan Road, Chicago, IL, United Statesrecommended Loyola University Chicago Lake Shore CampusI had a great time with my sister walking through the green yards, gardens and plazas of this tidy campus. It has a good bit of lakefront, so it would be a perfect place to bring a picnic lunch. We ... read morewere there on a rainy and very quiet Sunday, adding to the allure. Some buildings were open and we could peek in and even use the restroom.
- Bookman's Alley1712 Sherman Avenue, Evanston, IL, United Statesrecommended Bookman's AlleyThis warren of book rooms is tucked away in an alley in downtown Evanston. Visit soon, as the elderly owner is on the verge of closing shop. In additions to books he's collected all manner of ... read morememorabilia and quirky decor.Recommended for:
- American Science & Surplus5316 North Milwaukee Avenuerecommended American Science & SurplusIf you're a tinkerer, or maybe a geezer (I aspire to become one) or you just love parts and bits and tools and instruments at great clearance prices, this place is for you. Browse bins of drives and ... read morewheels, kits and models, motors and pumps, and even robot parts. It all screams potential. Conveniently located near O'Hare Airport.Recommended for:Budget Travelers
- Candlelite Chicago7452 N Western Ave, Chicago, IL 60645recommended Candlelite ChicagoCandlelite stands out on a windblown Northside street because of it's totally cool neon sign. (Photo to come.) Inside it's a combination of family pizza restaurant and neighborhood sports bar. I went ... read moreto meet a friend to watch the Cubs in warmth and comfort. I arrived first and felt at ease parking myself at the bar in front of one of the many LCD TVs and ordering my beer. My friend arrived and it was quiet enough to catch up on news and tell stories (jobs we had in high school). Hunger crept up around the 4th inning and we ordered a veggie pizza. Very good! Crispy crust, hot, with plenty of veggies. And during the last at bat at the bottom of the ninth, all the folks in the bar gathered around the screen to watch the final Cub strike out. Would I go there again? Heck yeah. And ya know, it's a long season. The Cubs still have a chance.
- Devon AvenueWest Devon Street and North Western Streetrecommended Devon AvenueDevon runs east-west on Chicago's north side. It's a great street to walk, full of ethnic shops and restaurants. Walking east from Kedzie you'll find an Orthodox Jewish neighborhood, then Russian ... read moreAmerican, Indian American, Pakistani, and Bangladeshi neighborhoods. I once had a great time shopping with my sister who was looking for silk sari pants. You might enjoy the Indian sweets shops.
- The University of Chicago5801 South Ellis Avenue, Chicago, IL 60637-1476
- Robie House5757 South Woodlawn Avenue, Chicago, IL 60637-1602recommended Robie HouseIf you don't have time to visit Oak Park and the Frank Lloyd Wright buildings there, you can still see one of the best examples of his iconic Prairie Homes within the city limits, in the Hyde Park ... read moreneighborhood around the University of Chicago. Restored to its original glory, this house feels magical once you step inside - from the street, everything is hidden from view. Guided tours are worth your time.
- Rookery Building209 South La Salle Street, Chicago, IL, United Statesrecommended Rookery BuildingA gem of a building in the southern portion of the Chicago Loop. Designed by Daniel Burnham and later the lobby was re-designed by Frank Lloyd Wright. Incredible detail throughout the whole building, ... read moreincluding the stair wells. If you are in the loop - peek your head in for a true treat.Recommended for:Gregory B. Schlough
This is a architectural gem. Make sure to sneak up the elevator to check out the stairwells... gorgeous detail and rich history make this building a beaut.
- The Signature Room at the 95th875 North Michigan Avenue, Chicago, IL 60611recommended The Signature Room at the 95thI could spend hours just taking in the breathtaking views here, which are probably second best to the views from Willis Tower. The cocktails are delicious, and not very pricey, so it's a perfect spot ... read moreto just lounge the night away. The restaurant is on the 95th and the lounge is on the 96th. You can get bites up in the lounge too. The view from the womens' restroom are incredible!recommended The Signature Room at the 95thThe Signature Room at the 95th offers the BEST skyline view of Chicago while diners enjoy a great meal. If you are not in the mood for dinner in the classy dining room I still recommend heading to the ... read morelounge for a couple drinks to go along with the magnificent view.
- Millennium Park201 East Randolph Street, Chicago, IL 60601-6530recommended Millennium ParkGreat place to spend an afternoon. Bring a picnic and spread out on the lawn. Unless of course there's a free concert going on there, in which case you're in for an even better treat. "The Bean" and ... read morethe "Water Towers" in the park will delight anyone of any age.Recommended for:
- Pilsen, Chicago, IL 60608Pilsen, Chicago, IL 60608recommended Pilsen, Chicago, IL 60608Chicago's Mexican neighborhood is a world away from the polished Magnificent Mile, and it's a ton of fun for precisely that reason. Great, cheap Mexican food and pastries, a terrific soundtrack in all ... read morethe shops and restaurants, and the terrific National Museum of Mexican Art.Recommended for:Local CultureEvan Roth-Howe
The El goes to Pilsen. Not sure if this is what you meant by "historical neighborhood," but it sure is interesting.
- Architecture River Cruise333 North Michigan Avenue, Chicago, IL 60601-3700recommended Architecture River CruiseIt's tough to get a great view of much of Chicago's notable architecture from anywhere besides the river. Also just a nice way to spend an afternoon on the water. The cruises depart close to ... read moreMillennium Park, which is well worth a visit itself.Recommended for:
- Blue Man Group ShowBriar Street Theatre 3133 North Halsted Street, Chicago, ILrecommended Blue Man Group ShowIt's a total experience of music, percussion, pantomime and out-and-out weirdness; and it's also some of the most fun you can have in the city of Chicago. The Blue Man Group is a delightful and ... read moreconsistently unexpected show, and if you've got a heart in your chest it's quite likely you'll leave the theatre tingling with seriously good vibes: No joke.Recommended for:Nightlife LoversMatthew Crompton
If you've never seen it, Chicago's a great place to do so. Good luck! ^_^
- Goose Island Brewpub1800 N Clybourn Ave, Chicago, ILrecommended Goose Island BrewpubBeer, beer, glorious beer! Since 1988 this brewpub in Lincoln Park has been making some of Chicago's best craft beer, and God bless. The accompanying pub fare (like gourmet mac & cheese, yum) tends to ... read morebe outstanding as well, with a locovore ethos.Recommended for:FoodiesMatthew Crompton
Amazing beer and good food here.
- Bahai TempleWilmette, Illinoisrecommended Bahai TempleThe oldest Baha'i temple in the world, and the only one in the United States, both the grounds of the complex in a northern suburb of Chicago, and the temple building itself, are quite lovely. Baha'i ... read moreis an inclusive, non-denominational religious faith, and the beautiful white dome of the temple with its extensive, intricate carvings is a great place for silent reflection and meditation. If you're looking for something a little different in the Chicago area, it's more than worth the visit.Matthew Crompton
Actually a bit north of the city in a nearby suburb, this is a totally different experience to what one normally thinks of as 'Chicago'.
- Art Institute of Chicago111 South Michigan Avenue, Chicago, IL 60603-6110recommended Art Institute of ChicagoIn a city that's home to an exceptional number of truly great museums, the Art Institute may be the best of all. The museum is home to so many famous pieces that it's facile to list them all, and kids ... read morewill enjoy the excellent armor court. An absolute must for any visitor to one of the world's great culture cities.Matthew Crompton
I always visit this excellent fine art museum at least once when I visit Chicago.
- Orange2413 North Clark Street, Chicago, IL 60614, United Statesrecommended OrangeMy favorite spot for brunch in Chicago, Orange (there are a number of locations) is a funky place with a fantastic menu. They've got top-notch huevos rancheros and french toast kebabs skewered with ... read morefresh fruit, but my personal favorite is the 'pancake flight', a sampling of four different stacks of silver-dollar pancakes that changes weekly. I recall a lavender-honey offering that blew my mind. A warning, though: the lines for brunch are often out the door.Matthew Crompton
Love the funky brunch menu here.
- Giordano's Pizzeria on Rush 730 North Rush Street, Chicago, IL 60611recommended Giordano's Pizzeria on RushIf you are visiting Chicago for vacation or just a weekend getaway, I highly recommend that you try "Chicago" deep dish pizza at least once during the visit. I haven't been to many pizzerias in ... read moreChicago, but Giordano's Pizzeria serves excellent deep dish pizza. The wait for a seat during lunch and dinner is proof of the restaurant's popularity and quality. Plan to wait at least 30 minutes to an hour for a seat, but the wait is worth it.
- John Hancock Center875 North Michigan Avenue, Chicago, IL 60611-1779recommended John Hancock CenterThe John Hancock Center is a "must see" in Chicago. Visitors have the opportunity to go up over 90 floors to an observatory that offers spectacular views of the city and Lake Michigan. After some ... read morescenic photo taking, visitors can head over to the Signature Room on the 95th floor for a nice romantic dinner in the dining room or to the lounge for good cocktails, appetizers, and conversations.