Cubs aren't in town... but the White Sox are, and they're playing the Astros. Go to the south side and watch Carlos Correa!
Chicago is my favorite city for outdoor running. Running Lake Shore Drive south from Lake Shore Drive & North Avenue Beach to the Loop is incredible. You could do it in reverse, too, but you wouldn't get the skyline views. I would use the El(evated) trains getting to/from either airport, but most everything else you'd be checking out can be done by walking/Uber. The El would also be your best bet to get to Wrigley.
Wrigleyville is cool even without going to a game. Go to the beach, then just walk around he city. There are sights almost everywhere. Summer in Chicago is GOAT.
Public transit is very reliable for the most part, and you can take the Red or Brown line south into town (Depending on where you are at). The Blue Line from O'Hare and Orange Line from Midway (depending on which airport you fly into) They run pretty regularly so you wouldn't have to wait too long. Uber's and Lyft cars are EVERYWHERE in the Chicago area so that as well is an option. Cabs are as well, so your options are there. You can get a 3 day CTA Ventra Pass for like $25(ish) which allow for unlimited rides on the "EL" trains and buses. The weather up here is finally getting better, so just any walking/running along the lake path is an absolute must. Especially south bound. Great skyline views along with LOTS of midwestern hotties to look at too If youre into skyline views, I would recommend trying to check out the Signature room in the Hancock tower. Its a bar thats literally 1 floor below the observation deck up there, but its free to get in. Sure the drinks and food is a little pricy but the price of a few beers offset the observation decks admission charge. In my opinion, the skyline view is better view from the Hancock tower over the Willis (Sears) tower Chicago is know for its neighborhoods and boy does this city have them. Old Town is probably one of my favs along with Lakeview. Wrigley is great in doses but since you're here for a short time it would be plenty. Cubs game if able Pequods Pizza Museums (Chicago has lots) get an Italian beef sandwich (Portillos, Al's beef) Lakeshore paths, going southbound Millennium park has good walking around Just ride around on the red/brown line. Its elevated and if you see anything you like, hop off! Signature room hole in the wall neighborhood bars you randomly find are the best Oh, and if you order a 312 beer, say "three-one-two". Just trust me, you'll get laughed at if you dont
You would be surprised, but yes tourists actually say that. Three-Twelve Three hundred Twelve Thirty-one-two Yes, I heard it said A LOT where I used to work. Every, single, day.
Listen to this man. Go to Pequods. My father in law From Chicago brings us one every time he comes to town. I walked out of Genos(two hour wait) , walked probably three miles, and ended up at Pequods, a day after I had it for the first time.
This. It's like a hidden gem for tourists because it's rarely ever mentioned to tourists for some reason, but the locals know about this place. It's the best IMO. If you want Chicago style thin pizza, hit up D'Agostino's in Wrigleyville. It's so good, one of my favorites. Hot Dougs for hot dogs. Also Portillos in River North, try the hot dog there as well as their burgers and Italian Beef. Food wise, there's an endless number of options.
My weekly plug for The Dawson. My favorite pizza place was The Silo in Lake Bluff, but that's way up north.
Kuma Corner for a great burger. Finally tried Ditka's last time I was in town in April, surprisingly good! Have a drink at the Billy Goat in downtown. Ronny's Original Steakhouse in downtown is a great greasy spoon for breakfast, all the hotels will recommend Wild Berry but you'll end up waiting for more than an hour most days to get something to eat.
everytime someone asks about Chicago I tell them to go on a food walking tour. There is a great company in Chicago (http://www.chicagofoodplanet.com/) that does it. You get a nice tour of a Chicago neighborhood and get to sample several foods from well known and not so well known (but still very good) Chicago restaurants.
Chicago summertime is like "go" time , people come out of winter hibernation.Plus the city is feeling it with 'Hawks , Cubs ? Just throwing ideas out there.....
Haha helps playing up that your from down under! There are some legit hot chicks matching up. Chicago - architectural boat tour was awesome, so was Mellenium park - the bean was awesome and Hozier were playing! Stuffed myself too!
I just came back from Chicago last week and spent 5 days and 4 nights. People are extremely friendly and weather was nice. Go in May to avoid the heat and snow. My wife and I tried a lot of pizza places and Lou Malnati's is simply the best. Don't forget to try Portillo's hot dogs. We also took a boat tour in downtown Chicago Riverwalk and had a blast learning about Chicago's architecture and history. Miracle mile is great for shopping along Michigan Ave. We also went to the Art Institute of Chicago (must see) and visited Cloud Gate at Millenium Park. You should try to have some local Garrett's popcorn too. We also went to a view good restaurants including one called Girl and the Goat - great foodie place. Night bars are unique. We crashed the Drake hotel and enjoyed cocktails and live music. Chicago is a huge sports town but I wasn't too interested in check out Wrigley Field. All in all, the place to visit in the Midwest.