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Guide To A Long Weekend In Chicago

You could never get bored in Chicago. It's the perfect city for a long weekend away and it can become whatever you want it to be, from relaxing and luxurious to adventurous and active. Here are a few of the most fun places to stay and eat and things to see while you plan your long weekend in the Windy City.
Longman & Eagle
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Longman and Eagle
2657 N. Kedzie Ave.
Chicago, IL 60647
(773) 276-7110

Whether you just go to Longman and Eagle to dine or decide to make it your home away from home for the weekend, you'll undoubtedly be charmed by its low-key atmosphere. Regular patrons enjoy the inexpensive and yet high-class whiskey, and the brunch served at the Longman and Eagle is oft praised. Located in Chicago's Logan Square neighborhood, Longman and Eagle is easily accessible off the blue line, however, it's not in the normal downtown circuit of hotels and therefore more of a local find. The hotel's tagline, "a modern take on an old Chicago neighborhood inn," pretty much sums it up.

Architectural Tour
Chicago's First Lady
112 E. Upper Wacker Drive
Chicago, IL 60611
(847) 358-1330

There are several cruise lines to choose from to take a boat tour on the Chicago River. The architectural tour is oft reputed to be one of the best both from Chicago natives accompanying their visitors and the first-time tourists themselves. The tour is an excellent way to rest your legs if you've been out and about taking in the city all day and you can still enjoy the nice weather and learn about Chicago's incredible skyline. You can book the tour in advance, which may be recommended for a high-activity day or walk up on a whim.

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Millennium Park
201 E. Randolph St.
Chicago, IL 60602
(312) 742-1168

Millennium Park is a must-see for those visiting the city, especially for the first time. It's beautifully put together in the heart of downtown and absolutely free. In the warm weather, enjoy wading in the Crown Fountain and watch playing kids try to avoid the streams of water spouted by the giant changing, smiling faces. Make sure to take a look at the nature walk paths, which are beautifully maintained and the flora is well documented. Check for a free performance at the Pavilion or just bring a picnic lunch regardless and enjoy it on the lawn. Of course, make sure not to leave the park without taking your picture by the Bean (officially titled Cloud Gate).

Related: Best Tourist Attractions In Chicago Worth The Hype

iO (formerly Improv Olympic)
3541 N. Clark St.
Chicago, IL 60657
(773) 880-0199

Why come to Chicago without taking in some of its famous improv comedy? There are several improv houses to choose from, but check out iO and you can take a look at Wrigley Field as you walk by from the red line, killing two touristy birds with one stone. The club has more than one stage and improv teams are almost always performing so chances are you'll be able to catch one at a time that's perfect for you. Prices vary by stage and group (higher-level students do perform) and you can look up a bit about each group beforehand or ask around if you'd like to make a more informed decision. Shows range in price from free to $14 making it possible to see more than one show without breaking the bank and, of course, there are full bars in both theatres.

Museum of Science and Industry
5700 S. Lake Shore Drive
Chicago, IL 60637
(773) 684-1414

It would be a shame to visit Chicago without at least checking out one of its amazing museums. Although you'll enjoy your visit in any climate, if you happen to end up with a more chilly or rainy day during your long weekend, check out the Museum of Science and Industry. With three floors of exhibits, both longstanding and new arrivals, there's bound to be something to interest everyone in your group. There's a submarine right inside the building for you to take a quick tour through and be sure to visit the coal mine that has also been in the museum for decades. Be sure to take some time to check out the amazing history of the museum itself, which is fascinating in its own right.

Related: Best Ways To Tour Chicago

Meredith Lyons is an actor, competitive fighter and fitness instructor in Chicago who also owns an amazing cat named Jake. Meredith has been writing on Examiner as the Chicago Martial Arts Examiner since 2008. Her work can be found at

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