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Erin
Salt Lake City

Chicago

One night in Chicago for friend's birthday - What to do?

I am thinking of surprising my best friend for his birthday by taking him to Chicago! We will only be there for one night (two at the most), likely near the end of October. Arriving around 7 pm, leaving the next day at 3 pm. What should we do?

We are in our mid-twenties. He likes beer, sports, atmosphere, and attractions unique to the city they are in. He has been to Chicago before, and loved it. He talks about how much he wants to go back all the time. He especially raves about the deep-dish pizza. I have been once when I was younger, so I don't remember much of it.

Where should we stay? I have looked at Magnificent Mile and the prices are... well, pricey. I am willing to spend the money if it is worth it, but I am wondering if getting a cheaper hotel and paying for the taxi rides will be cheaper?

What I am mostly looking for is giving him a good time, that's not too expensive, but one that he won't forget. My budget is about $300 for the hotel and activities. Thanks for the help!


4 Answers

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answered by
Dabs from Chicago

Friends of mine love using Priceline in Chicago, you get a much nicer hotel for a fraction of the cost.  Depending on the weekend, you can get something for well under $100 per night.  Check betterbidding.com or biddingfortravel.com.  You can also have a look at Hotwire, you can tell if it's a busy weekend by some of those rates.  There appears to be a mid size convention on the last weekend of October, maybe the rates will drop a little between now and then but I don't see much on Hotwire under $100 per night.

Are you game for a hostel?  There's a nice one in Lincoln Park, the Chicago Getaway Hostel, and there's one in the Loop run by YHA.

If really in a bind, you can stay out near one of the airports but that will involve a long el ride each way.

Pizza-my personal favorites are Lou Malnati's Pizzeria for deep dish and Giordano's for stuffed, there are multiple locations for both but I've marked the less touristy ones hence less of a wait.


Mentioned in this answer:

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  1. Chicago Getaway Hostel (hotel)
  2. Lou Malnati's Pizzeria (restaurant)
  3. Giordano's (restaurant)
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answered by
Susie from Chicago

In terms of places to stay, I would first recommend looking at airbnb. There are tons of options there for much less than the price of a River North or downtown hotel. Alternative neighborhoods to search in that you might enjoy are Lincoln Park and Wicker Park/Bucktown - they both have tons of restaurants, bars, and lively nightlife. If you don't want to do airbnb, my friend wrote this piece which might give you some unique & budget friendly options (especially the hostels) - http://www.huffingtonpost.com/lisa-lubin/the-most-unique-places-to_b_5045804.html

My favorite deep dish pizza is at Pequod's Pizza in Lincoln Park. For really good local beer try Revolution Brewing. My favorite beer bar is Links Taproom which is right in the heart of Bucktown, so there are plenty of bars and restaurants nearby. If he wants to watch a game while you're there, most bars in Chicago align themselves with sports teams, so google whatever team and you'll find a bar that will be playing that game! Enjoy!


Mentioned in this answer:

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  1. Pequod's Pizza (restaurant)
  2. Revolution Brewing (restaurant)
  3. Links Taproom (restaurant)
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answered first by
Leonard from Minneapolis

If he's into beer & sports, go to Harry Caray's Italian Steakhouse. Who has the best deep dish pizza in Chicago is a question that can start a war. Lou Malnati's Pizzeria. Giordano's. Home Run Inn Pizza & Family Restaurant. Any are fine. Check AirBnB for not too expensive places to stay. If you have a second night, Untitled is one of the coolest night clubs anywhere. Have fun!


Mentioned in this answer:

map
VIEW DETAILED MAP
  1. Harry Caray's Italian Steakhouse (restaurant)
  2. Lou Malnati's Pizzeria (restaurant)
  3. Giordano's (restaurant)
  4. Home Run Inn Pizza & Family Restaurant (restaurant)
  5. Untitled (attraction)
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answered by
Eric from Chicago

An awesome pizza and sports place is Pequod's Pizza it's definitely off the Mile.  Look at staying at the Hotel Lincoln or Longman & Eagle They are both tucked into neighborhoods and are much more unique than the "downtown" Chicago that locals avoid at all cost. Both places also have amazing brunch/breakfast restaurant within them or are not a far walk from some great places.  Longman & Eagle is in Logan Square which has a lot of up and coming restaurants and breweries (Revolution Brewing). Hopefully that helps. 


Mentioned in this answer:

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VIEW DETAILED MAP
  1. Pequod's Pizza (restaurant)
  2. Hotel Lincoln (hotel)
  3. Longman & Eagle (restaurant)
  4. Longman & Eagle (restaurant)
  5. Revolution Brewing (restaurant)
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