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Chicago
Weekend Vacation Getaway

Destination Overview

Anyone who has spent any time in Chicago quickly falls in love with this charming city. I lived there twice in my career and both my kids were born there, so it has a special place in my heart. Despite winters that can be quite brutal (ever been stuck in O’Hare in February?), Chicago has much to recommend it as a terrific weekend destination. You’ll find world class accommodations and dining, one of the best art museums in the world, a rich cultural tradition, the Cubs and Wrigley Field, Navy Pier, wonderfully diverse neighborhoods and in the Magnificent Mile, one of the best shopping stretches anywhere. Add a lakefront location (is there any other city that has urban beaches?), a gorgeous skyline, friendly Midwestern people, authentic Chicago Blues and that Saturday Night Live incubator, Second City and it will quickly go to the top of your “must see” lists.


 

Click picture to enlargeThe Wrigley BuildingThe Water TowerThe John Hancock Building

Making Your Travel Plans

To make your travel plans you can go to our Weekend Planner for all the contact information.

 

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Click picture to enlargeNavy Pier Ferris WheelView of Chicago from Navy Pier Ferris WheelThe Chicago River

Getting There

Chicago is accessible by air from virtually anywhere in the country. Rail service is also available from both coasts. NY to Chicago by train is about a 28 hour trip. Taxi from O’Hare $40-$50. CTA: $2.25. The CTA from O'Hare is fast, efficient and inexpensive.

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When To Go

I love Chicago at any time of year, but the plains and the lake can make winters brutally cold and August very hot and humid. Spring is probably the best time to visit. The weather can be quite spectacular, it’s not too crowed and the already friendly people are even more so after a long, tough winter.

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Getting Around

Taxis are abundant, public transportation is good and riding the “El” can even be fun.

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Accommodations/Dining

There’s no longer any need to roll the dice on where you stay or to settle and stay at a “safe” national chain. BestWeekends Travel Advance Team takes the worry out of where to stay when you go away.

The BestWeekends Travel Advance Team does all the work for you. We research each destination by scouring the guidebooks, articles, blogs, reviews and rating systems. Then we visit the destination and stay in the properties. Finally, we talk to the locals to be sure we didn’t miss anything. The result: we post on our site only the best of what we experienced. You can book with confidence knowing that “we’ve been there” and that no one pays us for a review. Inside see our Featured Properties.

When you are away on vacation, there’s few things worse than a bad dining experience. We agree, so we follow the same process for identifying restaurants as we do for accommodations, but with an extra step. We believe that the best dining experience has the strongest combination of food, ambiance and service. Good food is a given in our recommendations, but the best food in the world just doesn’t taste as good in a poor setting and the best setting with poor service just doesn’t cut it for us. The BestWeekends Travel Advance Team only presents those restaurants that meet our strict criteria. Mangia….enjoy! Inside see our Favorite Restaurants.

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BestWeekend' s Exclusives

After selecting our favorite places to stay and eat, we sat down and made a list of all the other things that would save you time and make your stay more enjoyable. The result is “Special Things” and “Good To Know, Good To Go,” BestWeekends Exclusives.

Special Things identifies unique, fun and romantic things for couples to do together in a particular destination. Good to Know is our list of the “best” of everything from breakfast to burgers, cocktails to after dinner fun and much, much more. Why stumble around trying to find the “best”….we’ve already done it for you!

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Don't Miss

  • Outdoor concerts in Millennium Park
  • Navy Pier
  • The Art Institute
  • Shopping on the Magnificent Mile
  • Wrigley Field

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Local News

Here's where you can find the local "scoop" before your Second City weekend. Newspapers: Chicago Tribune, Chicago Sun Times. Magazine: Chicago. Entertainment: Time Out Chicago and Metromix.

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