48 Hours in Chicago

48 Hours in Chicago is a foodie’s dream, with Michelin rated restaurants galore it’s hard to go wrong with a quick weekend trip. The Navy Pier although a little touristy has some amazing little spots and is a great spot to hit. Miracle Mile with it amazing stores and interesting history is a great walk. Hit up Wrigley Field for a Cubs game with a side of historic spaces. The nightlife is incredible, the food and drinks are not just sustenance but an experience. This weekend spot is well worth the trip!

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We have created the perfect packing list to get everything you need for your small town getaway into one lightweight personal item. Flights are getting more expensive, and carry-ons have become a charge for almost every flight. Getting everything you need into the perfect personal item is one of the best tricks to keep costs low.

Utilizing United’s major hub, Chicago O’Hare Airport, you can likely find cheap direct flights from your local airport.

Public transit consists of the L trains, and the CTA Buses, load up a Ventra transit card that works on both, jump on the Blue Line which runs all the way downtown.  You can purchase a 3-Day Unlimited Pass, which will make getting around that much easier, keep in mind you may have to switch between bus, and train to get to your destination. Google Maps is a great way to navigate and not miss a transit change.

Once you land you have unlimited options for hotels, I recommend if you are keeping the schedule tight find a good deal on a hotel downtown. Hotels.com is the perfect option for finding great deals.

Hotels.com: The Obvious Choice. Book now and save! Hotels.com: The Obvious Choice. Book now and save!

Assuming you land around lunchtime, you have to head to Millennium Park, and see the Cloud Gate (everyone calls it the bean, I mean it does look like a bean), go to the very center underneath, trust me. Grab a Chicago style dog, and take a walk around the park, there is almost always something going on during the weekend.

From there, I suggest you take a quick walk up to the Riverwalk and see some of the sights. You can either be a super tourist and take a taxi (or rideshare) to Navy Pier, or you can head over to Michigan Avenue (Magnificent Mile) to shop some of the most beautiful stores in the city.

Dinner: either Chicago it up with a Chicago Style Deep Dish, we recommend Giordano’s,  (beware the over-order it will fill you up, also check the website to order ahead as the line gets pretty long) or fancy it up with Girl & The Goat, Top Chef Season 4 Winner, Stephanie Izzard, worth the hype but get the reservation in advance lest you be waiting in the cold for a table.

If you still somehow have energy, J. Parker has a nice rooftop bar option, Howl at the Moon is a nice live music option, and if you are looking to mix beach into your city hit a tiki bar named Three Dots and a Dash. Head back to your hotel and crash.

Hotels.com: The Obvious Choice. Book now and save! Hotels.com: The Obvious Choice. Book now and save!

Official Day 1:

Hit up brunch at Longman and Eagle, and then head to a baseball or basketball game, in the iconic Wrigley Field or the United Center, haggle for seats outside or reserve in advance, whatever rocks your socks.

After that, the options for museums are plenty, The Art Institute, (American Gothic (think classic Americana pitchfork), and Georges Seurat (all those tiny dots are mesmerizing).  The Field Museum of Natural History is perfect for the dinosaur hunter in all of us. The Museum of Science and industry for the scientist in all of us, from an enormous submarine, to an amazing space exhibit which has two real space capsules, and everything in between. If animals are more your scene, The Lincoln Park Zoo or Shedd Aquarium might be more up your ally.

After all that walking, you will likely want to grab lunch, tacos are amazing at Mi Tocaya Antojeria, and then hit up a river or lake cruise, there are a ton of options, make sure to haggle with the vendors that try to sell you, and find the right cruise for you.

Head back to the hotel to clean up for dinner

Dinner: If you are feeling foodie, Alinea is Chicago’s only 3 star Michelin rated restaurant.

We were lucky enough to get a reservation, and I can tell you the experience is well worth it.  Make your reservation 3 months in advance. There are a couple of experience level options depending on what’s in your budget.

After dinner, you can head to the Willis Tower, one of the top 25 tallest buildings in the world, if you agree to buy a drink, you don’t have to pay the admission, well worth it in my book.

If you aren’t completely exhausted by all of that here are a few other places that are a bit off the beaten path but worth the trek:

Chicago Cultural Center, was opened in 1897 and is located in the Loop across from Millennium Park. It has a Tiffany glass dome which is amazingly gorgeous. It is features over 1,000 exhibitions and programs that cover visual, literary and performing arts.

Grant Park and Buckingham Fountain is a landmark and was modeled after the Latona Fountain at the Palace of Versailles. It is such a fun fountain to visit, and if you remember Married with Children then you will totally remember this fountain from the beginning of the show.

The Chicago Picasso in Daley Plaza is a sculpture by Pablo Picasso, located at 50 W Washington St. Chicago, IL 60602. It was created in 1967, it is 50 feet tall and weighs over 160 tons. Totally worth seeing, and considered a Chicago treasure by the locals.

Frederick C. Robie House is on the campus of the University of Chicago, in Hyde Park. The building is significant because it is a National Historic Landmark, built by Frank Lloyd Wright in 1909-1910. It is one of the greatest examples of Prairie School the first American architectural style. The light and wood creations that Frank Lloyd Wright imagined an ultimately built are always worth a visit and walk through because the style is so distinct.

Museum of Contemporary Art located at 220 E Chicago Ave. Chicago IL 60611. They feature both local and international artists. It was established in 1967 and is one of the worlds largest contemporary art venues. They have both a permanent collection and rotating exhibitions from many notable artists.

The Second City Chicago is a comedy club located at 230 W North Ave. Chicago IL and has so many alums that have gone on to start at SNL the list is endless. You can go there and enjoy a comedy show and maybe even see the next Amy Poehler or Tina Fey. Check out their website for tickets and show times.

48 Hours in Chicago is not a lot of time, there is so much to see and do, but hopefully this is a great jump off point for you and your group to enjoy the Windy City!