Chicago food and drinks can be expensive in the touristy areas (core of downtown, Millennium Park, The Art Institute of Chicago, and the Magnificent Mile). But you can definitely still see a TON of stuff by just walking through these areas as well. From the mains piers and walking along the lake to cutting over to Millennium Park there is a ton to check out that is totally free. I've headed up to the Lincoln Park neighborhood to grab beers and food, there are a number of places you can checkout on yelp to grab food and drinks around.
1.) Kingston Mines - Blues Dance bar.. and amazing music..i think cover charge is 15 bucks..
2.) Hofbräuhaus - German brewery place in rosemont..(close to the ohare airport)
3.) John Hancock Observatory is a pretty cool place to hangout in the night.
outdoors.. I don't know how the weather is going to be- but looking at how its now.. its going to be cold!
otherwise.. Kayaking on Lake Michigan , Cycling along the stretch on lakeshore drive are pretty good activities..
There is also a state park around 60 miles from chicago its called "Starved Rock State Park" its pretty cool for a good hike and nice natural caves to watch..
The Garfield Park Conservatory is a gorgeous nature escape in the city that's free and a great place to spend a couple of hours. It was one of my favorite places to go during the winter when it's bleak and grey and otherwise disgusting outside.
If the weather is nice, the Morton Arboretum in Lisle is amazing. It's probably a half hour drive or so from downtown without traffic, and I believe admission costs something like $10/person. It's enormous and you could easily spend a whole day there if you wanted to.
A lot of people enjoy the Chicago Botanic Garden as well, which is about as far out to the north of the city. It's feels touristy and is busier as a result. Pretty hard to find a quiet spot (unlike Morton Arboretum) in the whole complex especially if you're going during a weekend.
I should mention that the architecture boat tours that they do from Navy Pier are actually really fun. A great way to absorb the gorgeous architectural legacy of the city in 90 minutes.
You'll be spoilt for choice in terms of good food in Chicago, but much of the city's culinary legacy lies in the $$$$ sort of places. That said, some of my favorite "cheap eats" sort of places are:
Franks 'N' Dawgs for gourmet hot dogs and sausages -- as good as Hot Doug's in my opinion, without the wait.
Kuma's Corner for incredibly decadent burgers.
Johnnie's Beef in Elmwood Park for probably the finest example of the Italian beef that Chicago is known for. (I personally am partial to the "combo" which has an Italian sausage encased by the beef.)
El Pollo Vagabundo is a little off the beaten path in Northlake (a good detour if you go out to Morton Arboretum), but I recommend it to all of my out of town friends as it's seriously some of the best Mexican food I've ever had in the US, and this is coming from someone who now lives in Southern California.
Longman & Eagle is probably the least uptight and least expensive (but yet still one of the tastiest) Michelin-star rated restaurants in Chicago. Not hard to eat for under $100 for two. No reservations, so go early to avoid the wait.
Of course, no visit to Chicago is complete without a trip to one of the many locations of Portillo's, which serves the Chicago-style hot dog and some of the best fast-food burgers in the business.
Anywhere along the Chicago lakefront is great for being outdoors. Some of my favorite spots are Montrose Beach, Northerly Island, and Grant Park. They have bike rentals that you can ride for a decent price as long as they are returned to another sharing place within the given time frame.
There are so many bars and food in Chicago that I would not even know where to begin. I find it best to just to walk down the street and pick a fun looking bar. I am sure your friends could help you there.
If you have time, The Green Mill is a cool place. It is a little off the beaten path and you will need to take a cab or public trans, but it is a jazz club from the days of prohibition and Al Capone. Still has 1920s like decor.
Enjoy my city :)
Here are some cool / cheap places I liked to frequent when I was living in Chicago 2 years ago:
- Big Star - this place offers great Mexican food (get the queso fundito, pork belly or fish tacos) and awesome drinks. They have $3 bourbon pours of some great bourbon. This place gets SUPER crowded so get there during off hours.
- Violet Hour - this place is a speakeasy run by the people behind Big Star and is literally right across the street from Big Star, though you would not know it. Drinks are a bit pricier here (~$10-14) but it might be worth it to go and see the inside (kind of like entering Alice in Wonderland world). The drinks are also really unique.
- Revolution Brewing - this place has great beers are great prices and their bar food is pretty good and well priced as well. This place also gets busy so be sure to get there early.
- The Whistler - this is sort of like Violet Hour in terms of having a really cool drink menu but the atmosphere is more hipster and the space is less interesting. The drinks are cheaper here though! They frequently have live music / DJs here.
- The Map Room - This place is for you if you love beer. They have hundreds of beers at good prices and a free BBQ buffet on Sundays (not sure if they are still doing this). For non-beer drinkers, they have the typical selection of liquor as well.
Here are some other cheap / free touristy things to do (I agree with another poster that there is not too much in terms of outdoorsy stuff to do):
- Cloud Gate - This is super touristy, but also kind of fun and free. It is in Millennium Park.
- The Art Institute of Chicago - this is free on Thursday nights from 5-8pm. If you are in town then, just walk around outside. The architecture is awesome and they have some crazy art installations outside that you can see for free. I think other museums might offer similar deals, but you need to check with them.
- Cafecito - If you are going to be hanging around Millennium Park, check out Cafecito for cheap Cuban fare. I would sometimes walk 15 minutes each way to come here for lunch when I was working.
- The Signature Lounge - skip the John Hancock Observatory, and grab a drink here. The Observatory is located on the 94th floor and the Lounge is located on the 96th floor. The drinks are expensive, but definitely way cheaper than a ticket up to the Observatory.
Wrigleyville, right near Wrigley Field is a great place to hang out. Plenty of fun bars and cheap bars. Sluggers World Class Sports Bar is a really fun bar in that part of town that has dueling pianos on weekend nights and batting cages.
1. Eat pizza. At any restaurant or hole in the wall, whether it's deep dish or thin crust, it tastes like the ones you'd find in Italy.
2. Get up to the Willis Tower
3. Walk around Millennium Park You'll have yourself an album full of great photos from this place.
5. Rent a city bike. My friend and I found so many off the beaten road artsy places by just biking around the city.
6. Go to the many spectacular museums.
7. Take an architectural boat ride. A little pricey if you're not into architecture, but it has really great views of the city.
9. Get some Garrett Popcorn . Best popcorn I've ever had. There's always a line, but goes by fast.
10. Dinner at the Navy Pier
Hope this helped!
For some adventure in April, you never know how the weather is going to be with outdoor activities, so I'd recommend checking out the Willis Tower where you can walk out on a glass ledge 103 floors up. Yep. I had to crawl out on it as it was too scary, but a really fun experience! Hope this helps - enjoy!
Chicago has tons of outdoor street festivals. They can be $5 to $10 but you can also get in free. It is a suggested donation. Check out all the street fests in Chicago: http://www.choosechicago.com/articles/view/CHICAGO-EVENTS-FESTIVALS-2015-CALENDAR/1446/#May