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Trip List by kmcbride1979

Wrigleyville in a Weekend

24 May 2006  26 years on Chicago's Northside
4.5 of 5 bubbles based on 30 votes

You've been Downtown to the Sears Tower, Art Museum and Michigan Avenue. But to really see Chicago, travel out of the Loop to one of its many fine, cultured neighborhoods. This guide will give you a great weekend on Chicago's hip and fun Northside!

Wrigleyville blends the old with the new: original brownstowns mixed in with million dollar condos, immigrant families neighbor recent college grads, a McDonald's next to Wrigley Field. You can find everything you're looking for including shopping, original restaurants, outdoor adventures and nightlife in this friendly, fun-filled 'hood and this guide will take you through a perfect weekend!

  • Explore locations featured in this Trip List: Chicago
  • Category: Perfect weekend
  • Traveler type: Culture, Sightseeing, Shopping, Active/Outdoors, Never been before, Repeat visitors, Sports buffs, Beachgoers
  • Appeals to: Couples/romantics, Honeymooners, Singles, Families with teenagers, Large groups, Students, Budget travellers , Active/adventure, Tourists
  • Seasons: Spring, Summer, Fall
    Wrigley Field, Chicago, Illinois

    First up, check the schedule for a weekend game at the Friendly Confines and book your trip to Chicago. As one of the last remaining original ballparks, this is a must see. The neighborhood comes alive during games - inside the park and around it!

    Tickets: $15-$65

    BEST WESTERN Plus Hawthorne Terrace Hotel, Chicago, Illinois

    The perfect location for your Wrigleyville weekend is the Best Western on Broadway. You're walking distance from the park and a quick cab ride to the great locations on this list. The hotel is immaculate and staff is amazing. You're in the heart of Wrigleyville at this hotel.

    Hotel: $85-$400

  • 3. FRIDAY: Sweet Home Chicago
    Tango Sur, Chicago, Illinois

    After you settle into your hotel, grab a cab and head a couple blocks west to Southport and Roscoe. This is an up-and-coming area with great bars and shopping. Be sure to grab an Italian ice at Anthony's (Southport & Newport) as you walk. As the hunger begins to set in, head north down Southport, past Waveland, to Tango Sur.

    Tango Sur is an Argentinean steakhouse (with chicken and veggie entrees too) and BYOB establishment. Yes, bring your own liquor. You'll see everything from friends sharing their favorite bottle of wine to a couple with a 6-pack of Coke and a bottle of Beam. So, bring your alcoholic beverage - or 2 - (you can stop at the Osco Drug at Southport & Waveland) and get ready to be served warm bread, chimichurri sauce and the tastiest entrees around. This is an absolute neighborhood fave and there may be a wait to prove it! But, put in your name and head across the street to Blue Bayou's beer garden for some drinks ($5 martinis on Friday) while you wait...and it's WORTH the wait!

    Dinner: $15-$25 per person

  • 4. FRIDAY: After Dinner Music
    B.L.U.E.S., Chicago, Illinois

    After you've enjoyed your delicious dinner and drinks, hail a cab to B.L.U.E.S. Chicago on Halsted. This is a true Chicago blues club and plays host to some of the best talent in town. Located across the street, and if you're still up for more music when the bar closes, Kingston Mines opens up and picks up where B.L.U.E.S. left off.

    If a blues club isn't your scene, another great spot for live music is Pop's for Champagne, a jazz club. Pop's is a swanky joint known for their delicious martinis and amazing music. After dinner, have the cab drop you at Pop's at Sheffield & Oakdale. www.popsforchampagne.com

    $10 cover charge at each venue


    Since you'll be heading to the game on Saturday OR Sunday, these two days are
    interchangeable. Here, I'll describe the perfect game day:

    Walk north to Addison from your hotel, then head west on Addison to Clark. Stop at Salt and Pepper Diner for a great, greasy spoon breakfast and even better Bloody Marys. You're directly across from Wrigley at this point, so you can watch the neighborhood festivities beginning to form.

    After you've satisfied your taste buds, head south on Clark and check out some of the great stores and restaurants. Be sure to stop at Strange Cargo, near the corner of Clark and Roscoe. Even guys like to shop here - they have over 200+ screens on their walls and blank t-shirts in every color. Pick from a Mick Jagger's 70's concert to a TransFormers to an old-time Cubs screen and they'll iron it on to a shirt - ready to go in 10 minutes. No cell phones allowed inside and you might mistake a worker for a fellow shopper in this laid-back store, but it is a definite "Wrigleyville" establishment.

    Shirts: $15+

  • 6. BASEBALL DAY: Before the game...
    Sport's Corner Restaurant, Chicago, Illinois

    After enjoying Clark Street by day, head back to Clark and Addison and walk just past the park to Sports Corner Bar & Grill. Rated one of Chicago's Top 20 Sports Bars, this is definitely the place to head before a game. Good eats, great beer and a very large space to house the fans before the game. You have a view of the field and outdoor seating so even if you start to have too much fun here, you'll be able to know when its time to head over to see the start of the game!

    Food: $8-$15

  • 7. BASEBALL DAY:...after the game

    Follow the masses south on Clark Street after the game to Slugger's. This is another great sports bar - after most games you'll get a chance to drink with Minnie Minoso (former White Sox) and Ronnie Woo Woo (the Cubs "mascot") both regulars. Most nights there's live music or dueling pianos. But don't get too cozy downstairs - be sure to head upstairs where there are batting cages to practice your swing and continue with the baseball spirit. When you've had enough of baseball, you can continue to bar-hop south down Clark Street. There's over 25 restaurants and bars, all ready to show you a great night out!

  • 8. BASEBALL DAY: When the Moon Hits Your Eye Like
    Chicago's Pizza, Chicago, Illinois

    A big pizza pie - is what you should get - after the game and night out. Chicago's Pizza, another Northside favorite, delivers throughout Wrigleyville until 4am! Local trick: On the cab ride back to our hotel call for delivery. When you arrive back at your hotel you'll have some fine Chicago-style 'za waiting for you. (I like the bacon best...)

    Pizza: priceless


    Today will be a day to experience Wrigleyville outside the stadium. Start by enjoying breakfast at a local fave (and across the street from your hotel) Ann Sather. The breakfasts are delicious and come with their infamous doughy, sugary cinnamon rolls. Mmmm....

    Breakfast: $8-$15

  • 10. NON-BASEBALL DAY: Outdoor Adventures

    Grab your walking shoes and beach attire! Your hotel is next to Treasure Island, Oprah's favorite grocery store. Go in and grab the makings of a picnic and head to Lincoln Park. Walk south on Broadway to Belmont. Head east on Belmont down the pedestrian path. This path will lead you from Lincoln Park down to Chicago's Southside! You can make this outdoor adventure as simple or as complex as you like.

    Start with a picnic at the breakers. As your walking down the pedestrian path, to your left you'll see Lake Michigan and people hanging around some rocks. These breakers are a great place to watch boaters, picnic and relax. You can either head back after this, or continue down the path you were walking. About a mile down you will hit North Avenue Beach. This is the best beach in the city (and where Jennifer Aniston and Vince Vaughn filmed all last summer). You'll notice it by the insanely large beached cruise ship. Hang out at the beach, do some people-watching or join a game volleyball. For lunch, head to the top deck of the cruise ship - Castaway's - for a great view of the city and some grub. Most afternoons there's also live music.

    Beach: free
    Lunch: $10-$15

  • 11. NON-BASEBALL DAY: Keep on going like a Northsider
    Lincoln Park Zoo, Chicago, Illinois

    If you want to continue to be an aggressive Chicagoan, head over the North Avenue Bridge to Lincoln Park. Here you will find the entrance to the Lincoln Park Zoo. The zoo is free and houses everything from polar bears to elephants and koalas to giraffes. Give yourself at least 2 hours to roam around this natural, friendly zoo. At the Lake in the Zoo there's paddle boats in the shape of swan's that provide for a relaxation on the water after your long day of walking!

    With that said, head back to your hotel, via cab at the entrance of the zoo.

    Zoo: free
    Swan Ride: $10

  • 12. NON-BASEBALL DAY: Mangia!
    Piazza Bella, Chicago, Illinois

    You've had your 4 of your 5 major Chicago food groups: greasy spoon, hot dogs,
    beer and pizza. Now for Italian! At the west end of Wrigleyville is an area named Roscoe Village. Here you will find Piazza Bella, a quaint Italian trattoria, a quick cab ride from your hotel to Roscoe & Damen. Food is excellent; service even better. You'll feel you've left the city behind and been transported to Northern Italy.

    Afterwards, you can head to one of the many bars on Roscoe for additional fun.

    Dinner: $15-$25


    This itinerary will keep you busy on your Wrigleyville Weekend, but to add one more of Chicago's finest, check out the above website to see what festivals are in town. Chicago celebrates throughout the Cubs season with different food and culture festivals - one that might coincide with your trip to the Northside!