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Old 04-17-2011, 09:08 PM
 
125 posts, read 636,701 times
Reputation: 55

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Hello All!!

My best friend and I are planning a trip to Chicago this summer. I am a 27 y/o female and he is a 28 y/o male. I really need assistance with the following:
(1) Best weekend to come (I know there are many events in Chicago and assume some weekends are better than others). Our options are May 26-29 (Memorial Day wkend); May 12-15; June 9-12; June 16-19
(2) Best location/part of town to stay.

Info to help:
- We are visiting to 'see the town' and relax... not really into visiting museums or historical sites... we moreso want to eat good, walk the city, and enjoy the nightlife.
- We are buying the flight/hotel via a discount website in a bundle package... so its tough to list a hotel/night price. But lets say that budget is less important... the most important thing is that the hotel is in a great location... "Walkable" is best... or a short cab/train ride to restaurants, nightlife, etc.

And only last random (selfish) request... is there a nice authentic Cuban restaurant in Chicago? I love Cuban food and always try to get some in a new city.

Any assistance would be greatly appreciated!!

Thanks in advance!
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Old 04-19-2011, 08:26 AM
 
Location: Wicker Park/East Village area
2,474 posts, read 4,173,356 times
Reputation: 1939
Chicago Area Guide | Days Inn Lincoln Park | Chicago, IL
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Old 04-19-2011, 08:59 AM
 
Location: Houston
279 posts, read 760,739 times
Reputation: 157
Quote:
Originally Posted by AtlantaGal View Post
Hello All!!

My best friend and I are planning a trip to Chicago this summer. I am a 27 y/o female and he is a 28 y/o male. I really need assistance with the following:
(1) Best weekend to come (I know there are many events in Chicago and assume some weekends are better than others). Our options are May 26-29 (Memorial Day wkend); May 12-15; June 9-12; June 16-19
I'd say the later in summer the better to increase your chances of warm weather. May can still be hit or miss, but June should be warm. Beyond that, check out which festivals are going on during the weekends you're considering and pick the one that has things going on that interest you more. Here's this year's festival guide:
Chicago Festival Guide 2011 | Metromix Chicago

Quote:
(2) Best location/part of town to stay.
I'd recommend something downtown, specifically in River North, Magnificent Mile, Streeterville, Gold Coast, or Theater District areas. Any of those should work fine and will put you in walking distance to tons of entertainment and restaurants as well as the trains. I don't recommend staying in the Loop unless it's the far north edge of it (Theater District) because that area more or less shuts down after business hours.


Quote:
And only last random (selfish) request... is there a nice authentic Cuban restaurant in Chicago? I love Cuban food and always try to get some in a new city.
90 Miles Cuban Cafe
Cafecito
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Old 04-19-2011, 10:00 AM
 
1,210 posts, read 3,065,681 times
Reputation: 651
As OrangeAndBlue said, stay somewhere on the near north side if possible. You might be able to find a place a little bit cheaper right in the Loop but it won't really be right in the mix of things in terms of food nightlife.
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Old 04-20-2011, 03:38 PM
 
14 posts, read 25,579 times
Reputation: 14
Hmm, it's not like getting from South Loop to River North exactly takes a very long time... and if it's cheaperr to stay there, I don't really understand why it's such a bad idea for these two
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Old 04-20-2011, 03:51 PM
 
Location: Tower Grove East, St. Louis, MO
12,063 posts, read 31,652,770 times
Reputation: 3800
^Sure but River North is then close to a lot of the other great neighborhoods on the north side. I always hope people get off the mag mile and really see the city. The first time I came up here was just for a long weekend, and I wish I would have gotten a chance to explore more, but I didn't know where I was going! And the el overwhelmed me haha!
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Old 04-20-2011, 09:28 PM
 
Location: USA
5,738 posts, read 5,451,650 times
Reputation: 3669
Anywhere further on the North side is great to stay. Downtown is dead during the day and River North is for tourists and rich people. Based on what you've said, I think you'd really enjoy being able to step outside of your hotel and be where actual Chicagoans live and hang out. The neighborhoods east of the river are all nice, if a little fluffy, and I do recommend going west and making a stop in Wicker Park.
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