CHICAGO: Cheap Hotels in Chicago
Chicago attracts large numbers of visitors with its theaters, restaurants and good shopping centers. Chicago hotels come in all shapes and sizes and there are a good number all around the city.
When to visit based on priceYou’ll find your best rates between January and March during winter months.
Key attractionsChicago is famous as the town of Gangsters for a reason, because it’s history is full of organized crime. So what better to do when visiting than by taking a Chicago Gangster Tour? You will visit Mount Carmel Cemetery where you will visit Al Capone’s final resting place and the Biograph Theater where the infamous John Dillinger was gunned down.
Make a stop at today’s tallest building, the Willis Tower in downtown Chicago. And during the day or especially at night, view the Buckingham Fountain and it’s spectacular light show. You’ll never forget the beauty of this fountain, with its four horses.
While at the very top of the Willis Tower, test your nerves of steel by stepping out on its Skydeck Chicago. This is a clear glass ledge, totally enclosed, but with a glass floor also. Might be advisable to do this before lunch.
Combine fun and one of Chicago’s premier attractions visiting Navy Pier. This lakefront fifty acres of fun features rides, restaurants, museums, gardens and so much more. Especially popular is the 150-foot Ferris wheel that operates all year long.
Having funThere are two excellent museums in Chicago, the Field Museum and the Chicago Museum of Science and Industry. Another great place to visit if you’re interested in fine art is the Art History Museum that houses the biggest collection of Impressionist artwork in the United States.
If by chance you are visiting during the summer, for sure check out he free Outdoor Summer Concerts at the Jay Pritzker Pavilion.
If your thirst for experiencing the old days of prohibition, then find your way to the old “mob” hangout, and oldest “speakeasy” in Chicago. We’re talking about the “Green Door Tavern” on New Orleans Street. This is an excellent opportunity for you to try one of their prohibition-style drinks and possibly some lunch or dinner. It’s still a very popular hangout, so keep an eye out for Machine Gun Kelly and his gang of thugs.
ShoppingYou’re in Chicago and looking for the best shopping area. Hands down you should head to the Magnificent Mile Shopping District. This strip in downtown Chicago is chock full of history, lying between The Michigan Ave Bridge and Oak Street.
Here you will find yourself entertained with days of shopping in brand name boutiques, mega malls, luxury outlets and retail stores lining the street.
There are three-mega mall that you shouldn’t miss on your quest for packages. The Shops of North Bridge, 900 North MichiganShops and the Water Tower Place should be your target.
NearbyA truly awesome experience is a day trip to “Starved Rock” where you get to walk some forty plus nature paths overlooking one of Mother Nature’s canyons.
Why not take a trip to Milwaukee, which is only about an hour and a half drive. Visit the home of the Harley-Davidson Museum; sip a beer on the tour of the Pabst Mansion.
You can also take a drive to Lake Geneva Wisconsin, a very popular resort town where you can hang on the beach or maybe take a cruise on a paddleboat on the lake.
Another interesting way to spend a day is to visit Amish Country in Indiana; only a couple hours drive away. Some very interesting shopping with homemade pies, quilt shops, jams, etc. It’s a great experience for young children and quite the education for adults too.
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Tips for a great Chicago Family Vacation
If experiencing Chicago from the ground is your cup of tea, and maybe the kids need to burn off energy, hit the Chicago Riverwalk. Start your stroll at the Clark Street Bridge and walk along the lake, or rent bikes or roller blades if you want. In nice weather it’s also possible to rent kayaks and the lake is super for cruising with the family.
Combining your vacation with a bit of schooling adventures should excite your children, the moment they walk through the door of the Field Museum. Even adults are amazed when they stand in front of “Sue”, the best-preserved and largest skeleton T-Rex in the world today. There are hours of displays and interactive games for youngsters and oldsters alike.
Visiting Chicago with children almost requires that you visit the Shedd Aquarium, especially in summer just to get out of the heat! The Shedd will amaze boy you and your children, with over 32,000 animals represented, including sea otters, whales and dolphins. Make sure you put this at the beginning of your day, so you don’t feel crowded or rushed at your favorite exhibits.
And then there’s a no-brainer, a day at Navy Pier. From the carnie food, games to exciting rides and mega Ferris wheel, it’s always a good day to visit. Be sure to take the time to visit the Children’s Museum, because it’s one of the best. A bonus for 2017, Cirque Shanghai is performing on the Pier until September.
Especially for families traveling with small children, the LEGOLAND Discovery Center Chicago has some of the best re-productions of famous Chicago attractions, built from Lego’s. Navy Pier, Willis Tower, Wrigley Building and more built from thousands of tiny Lego’s. Your children can take a factory tour, Kingdom Quest Laser Ride, Jungle Expedition and so many other new adventures. Of course, you can take a break and munch out in the LEGO Café, or save a bunch of money, grabbing Chicago Dogs from the cart on the street.
You don’t have to be a baseball fan to enjoy the game, and nothing says baseball more than catching a game in Wrigley Field. Built back in 1914 you will find this stadium untouched like many others, with “luxury suites” and electronic scoreboards. Show the kids a real ballpark, where the scores are updated by hand, but they still serve the best dogs and beers. If you decide to catch a game, get your seat tickets early because they sell out. Also I suggest a day game, without the heavy boozers at night.
If you are lucky enough to visit during the summer months, you need to take the family to the beach, consisting of 29 miles of shoreline with more than 15 miles of beach. Surround yourself with locals, and while mingling, get some ideas on best family restaurants, and possibly best “happy hours” for you two after the kids are asleep?
Hot money saving suggestions for your 2017 Chicago vacation
As far as eating smart, if your hotel doesn’t offer free breakfast, try hitting a coffee shop for breakfast instead of fancy restaurant. Even eating at Starbucks will be cheaper than in the hotel restaurant.
Money tip: Bring cash instead of paying ATM fees. Just be smart and use the hotel safe for some of it.
As far as choosing your hotel for vacation, besides looking for a deal, you should try to choose one in the vicinity of the attractions you plan to visit if possible. If traveling with the kids, maybe choose something near the museums, Navy Pier and such. Adults want to check downtown near the shops, restaurants and of course nightlife.
Something I always try to do is bring a really good bottle or two of favorite wine with me, anywhere I travel. Even if the restaurant charges a “corkage fee”, its way cheaper than the cost of a great bottle of wine from the restaurant wine cellar.
Hot Wine Travel Tip- shop and buy one of the bubble wrap sealing wine bottle holders ahead of your trip.
Both young and old will enjoy spending time on Navy Pier, riding its iconic 90 foot Ferris wheel, great restaurants and even scenic boat tours. If you like old stained glass, there’s a free stained glass museum on the pier.
Lincoln Park Zoo is another great place to visit, check out the animals, and best of all, it’s free.
You can check out a ton of popular attractions and still save bucks by purchasing a Chicago CitiPass for only $98. Check out the Skydeck Chicago, Shedd Aquarium, Museum of Science and Industry and much more with it.
If there are museums on your “must see” list, check out their free or discount days and hours. Many including the Shedd Aquarium, Adler Planetarium and others offer specific days of free entry.
Now for my suggestions for saving money on lunches and yes, even dinners if you are brave. Chicago is well known for two food groups, their Chicago Dogs and Chicago Deep Dish Pizza. You can keep to a great lunch budget on hot dogs, and pizza, great for lunch dinner, and leftover for breakfast too.
Chicago “spring break tips” for singles, couples and families
Another way to save money, see more of the countryside and meet interesting people is to jump on a Greyhound or Mega Bus. Certainly long trips via bus aren’t always enjoyable, but if your just traveling a state or two, why not save money that can be used on your vacation.
And the savings don’t stop there, because if you use public transportation around town, you won’t need to rent a vehicle. Taking the “L” train is actually one of the best ways to get around the busy city. Easy to figure out which train to use because they are all color-coded and offer a map. Also, if you want to get out of the city, you can also hit the suburbs on the Met Line.
And then there’s a third mode of transportation you probably never thought of, by boat! No you don’t have to buy or tow your boat to Chicago, they actually offer Water Taxi’s in addition to regular taxis. You can catch the water taxi service along both Lake Michigan and the Chicago River.
Now, if you really want to save some money on transportation as well as work off dinners, why not rent a bicycle? There’s a system called Divvy located in hundreds of locations around the city. You can eliminate the traffic frustration as well as everyday parking spot nightmare. Pick one up in one place; turn it back in at another. Each location offers maps so getting lost will be minimal.
As far as seeing the popular sites in Chicago, there’s no better way than by purchasing a Chicago City Pass, costing under $80 for children and under $100 for adults. You may think this kind of expensive, but if planning on visiting the major places like Shedd Aquarium the Skydeck, Science and Industry Museum and more, it will save you on admission fees. Plus, there’s the fact that you get express entry, passing the lines.
Whether a couple on a romantic escapade or couple traveling with ten kids, we have one suggestion for a dinner that works for all. North Pond, a restaurant located within the original “warming house” for the park ice-rink built in 1912 is the bomb!
It just might be the right place for that one big splurge. The restaurant is located within Lincoln Park and offers one of the best skyline views of Chicago.
Finally I have to say that with the warmer weather coming into spring, it makes visiting Chicago’s Navy Pier much more enjoyable. Fun and games, food, arts and crafts and of course, the Ferris wheel awaits you, if not just for a great selfie.
Awesome day trips from Downtown Chicago this winter
While we are talking about Wisconsin, we need to also look at day tripping to one of the brew ha-ha capitols of the West, Madison, which is one party college town. From the Old Fashion Pub in downtown to Capitol Brewery and Wisconsin Brewery, the suds will pour well. This is always a cozy way to spend a day, hitting a few of the famous Wisconsin breweries and their tours.
Maybe you are in the same mind as many locals and just want to get out of town and relax. What better way to do that, than to escape to where locals do, the Lake Geneva, Wisconsin spas. Traveling just an hour and a half from downtown Chicago, puts you in a winter wonderland of snow, trails, pubs, and of course the lakefront spa. In fact, there are many spas to choose from, so after an hour or so walking trails and taking photos for future holiday cards, head to one and get “stoned”! We’re talking about “hot stones that is.
So who has not ever fantasized jumping on a sled behind a team of huskies and yelling “mush”? Well we have your opportunity, and its only about a two hour drive to Elkhart Lake, WI, and the Siberian Outpost Dog Kennel, where you can ride with a guide, or actually learn on the job. That isn’t the only form of entertainment available, because there’s excellent ice- skating and sled rides too.
Of course, after a day out in the snow and cold weather, you deserve a stop in the Resort Pub for a warm cocktail.
Finally we have the ultimate escape from Chicago, to a place only Olympians have gone before you. When you sat in your warm living room, watching the Olympics, and the exciting ice luge downhill runs, you told yourself that you could do that. Well, here’s your chance to do just that. There are only four official ice luges in the United States, and there’s one only three hours drive north away for some supreme excitement. The Muskegon Winter Sports Center offers a beginner ice luge for you to slide down. Don’t smile when we say a “beginner slope” because you will be flying 30 mph!
Winter fun ideas for family vacation in Chicago
For some outside adventure and yes, exercise as well, how about tying up some skates and hitting the McCormick Tribune outdoor ice-skating rink wiring Millennium Park. Mom and Dad can choose to hit the ice with the kids or relax on a bench with a cup of hot chocolate and watch. Skate rentals are really cheap and worth the photo’s of the kids anyway.
Chicago enjoys some excellent World Class Museums and supply hours of indoor time for you when the outdoor weather gets too much.
The Navy Pier is still a great place to hang out and even though you might have to bundle up, provides lots of activity. For the little guys you have the Chicago
Children’s Museum there also with activities for all ages. Another top attraction is also great anytime during the year, and that’s the Shedd Aquarium. The experience for the whole family is outstanding, with eight exhibits to visit. The Polar Play Zone is quite entertaining, as is the white-sided dolphins, sea lions and otters in the Abbot Oceanarium. The Caribbean Reef lets you experience the under sea wildlife of the blue waters of the Caribbean. And then there’s the Wild Reef with sharks, sharks and the more sharks.
If you and your youngsters enjoyed
Night at the Museum” together, you can surly have a ball touring the Field Museum and its exhibits. The museum features many of the animals from the movie, including dinosaurs, African animals, and even Voodoo dolls. If your visit is in January or February, you will have the option of visiting the museum after dark.
The museum is offering special nights when they will open the doors all night long. You will get to walk the exhibits with only a flashlight to see with. Now that’s living the dream for “Night in the Museum fans”.
Now we have something really fun and challenging for you to take your kids to. Its located in the Museum of Science and Industry, and before you start thinking “boring”, let me give you a clue. Do you remember the hedge maze in the movie “The Shining?”. You may want to do this one with your youngsters. It’s a 1,000 square foot mirror maze! And what’s even better, there’s a hidden room in the center. Are you up for the challenge?
Free, Cheap and Fun things to do on your Chicago Vacation
Fun Fact: From Memorial Day until Labor Day every Wednesday and Saturday night there are free fireworks over the Navy Pier waters.
Another free option for activities or just a relaxing picnic in the park is Chicago’s Millennium Park. During the summer months bring the little ones and let them splash in the wading pools. Check out art displays, free outdoor concerts or just relax. During the winter months the main plaza in the park transforms into one large ice-skating rink. If you plan ahead and bring your blades, its free to skate, and if not you can rent them for $10.
Another fine day on your vacation could be spent at the Lincoln Park Zoo, hosting well over 200 species from the animal world for your viewing pleasure. This is where you get up close and personal with big cats in the Kovler Lion House, Polar Bears, Monkeys, Flamingo’s and reptiles and more.
Is there anything more fun and cheap than grabbing a famous Chicago Dog or Chicago Deep-Dish Pizza for lunch? These are Chicago traditions, and why not live like a Chicago resident for a while?
There are pizza joints everywhere, but we have some tasty selections for you to choose from. Giordano’s is local famous for their stuffed pies, while Lou Malnati’s boasts fresh mozzarella cheese from the same dairy for the past 40+ years. Foe a fun experience and awesome pie slices, check out The Original Gino’s East, where everyone gets the opportunity to write something on the wall, ceiling or wherever, plus the pizza is boss.
For your sit down or grab and go dog, Chicago-style, head to Portillo’s for one of the very best dogs ever! If you take our advice and visit Lincoln Park, the Chicago Dogs at The Wieners Circle are sweet!
If the series Boardwalk Empire and Gangsters has gotten your interest, why not take a selfie in front of the Biograph Theater, where in 1934, John Dillinger was shot?
After all, it’s free.
Here’s a “hoppy” idea for adults that involves sipping micro-brew beer and a free tour. The Revolution Brewery offers free tours every Wednesday –Friday that takes about 40 minutes along with two beer samples. Of course, if using public transportation, help yourself to a pint or two at the bar after the tour.
“Chilling Out” in Chicago this summer
Chicago proper offers many options for my kind of chill, and here are some of the top choices for locals that you need to check out.
First on the list is Jeni’s Splendid “ artisan-style” Ice Creams where Jenni and her crew use local grass-fed mid-west milk for their “brew”. Their creamy milky flavors come from the Dutch chocolate and authentic Ugandan vanilla beans. Your kids might just go bonkers over the wildberry lavender ice crème, and adults, wrap your lips around a shot of whiskey ice crème.
If memories of a vacation in Italy bring back sweet memories of Gelato, stroll into one of the Black Dog Gelato shop’s hat have all but become the craze for local Chicagoan’s. For over our years these guys and gals have been perfecting their creations of weirdness, but cool. Nutella and pretzel, apple cider and brown sugar and cinnamon will give you a clue of what’s coming to your palate.
Frozen yogurt shops are everywhere, but our personal favorite is Forever Yogurt, the very first of its kind to offer Froyo with those beautiful swirls. Flavor and toppings are to many to quote, and options like Italian Ice and the new addition of Fronada, like a DQ Blizzard provide quite the menu.
Now that you’ve chilled off a bit, why not head out to one of Chicago’s sandy beaches and spend some time in some cool lake water. Here is a review of some of the top beaches where you can soak up some sun and jump in for that refreshing chill.
Probably the most popular of beaches is North Avenue Beach with its “ocean liner inspired” beach house. Rentals are available for all kinds of water activities, along with food vendors when hunger strikes.
The Montrose Beach is the place to head to if you have Fido on vacation with you, because its dog friendly and your pup can run and play with others.
On the South Side of Chicago there’s Rainbow Park and Beach, so you have the best of both worlds. If you have a cooler with you, you can hit the waters and beach, and enjoy a midday picnic in the park.
A great idea for getting out of daytime heat for a couple hours especially if traveling with young kids is a visit to the John G. Shed Aquarium. The Shedd has been entertaining both locals and visitors for almost eighty years. Visit the Amazon in Chicago, with snakes, piranhas and more. A few years ago renovations brought a tide pool and created river and even the ne otter-habitat. Just the air-conditioning is well worth a visit.
Your “cheap eats” bucket list for visiting Chicago on a budget
Our first locals recommend for Sunday Brunch is Chief O’Neill’s Pub & Restaurant.
This pub offers an excellent “All you can eat buffet brunch” from 10am – 2 pm on Sundays. You pay less than $20 per adult, and youngsters 10-18 years old for $14. Little ones under 2 years old are free. On the menu everything from egg dishes to Fish & Chips, shrimp, Smoked Salmon and Calamari, beef and an “omelet station”. Finish it off at the ice crème station. Getting hungry yet?
Another top spot for hungry locals is Jane’s Restaurant located on Cortland St. This restaurant was voted Chicago’s most romantic for evening dinner, and is surly a excellent choice for their famous brunch, served Friday through Sunday. There seems to be almost an endless choice of food choices here, with starters like special Caesar Salads and corn chowder, to sandwiches, Salmon and pork belly, Three Eggs benedict (my personal favorite), pancakes and so much more. They also offer a special children’s menu.
For dinner we have two awesome experiences in dining for you that won’t break the bank. The first is Blue 13 that serves up American cuisine every Sunday at a very affordable price. How do three courses for $20 per person sound to you? Everything is fresh from the farmers market and juicy delicious herbed chickens and greens. Keep in mind that if you are a big eater, seconds is permitted if you can take another bite. Located on West Ontario Street, this is a local choice, and should be on your list also.
Finally we have a dinner suggestion that you would imagine should be listed as “fine dining $$$$”, but it isn’t. Café Des Architectes is owned and operated by Master French Chef Martial Noguier. What he will present to your table Sundays through Tuesday in his “Neighborhood Friends Special Menu”, is an experience you will not believe. He offers his French delight 3-course dinner for $29 per adult, $16 per youngsters 6-10 years old. From his fennel Salmon Tartare, Flatiron steaks and more will tantalize the taste buds. For the experience he offers his “neighbors” you will feel part of this neighborhood, and experience dining as locals do.
Planning a visit to Chicago? Careful planning can save a bundle!
One of the top destinations for visitors to Chicago is the Navy Pier, located on fifty acres of fun and adventure. From amusement rides, shops, restaurants to beautiful gardens to explore and so much more, you can easily spend a day here. It costs nothing to get in and is a special place to walk the boardwalk, and catch that perfect photo of the Chicago horizon. Stay into the evening and enjoy the free fireworks every summer evening from Memorial Day until Labor Day.
If you’re ok with a bit of exercise, then have we got an adventure for you, and again, it’s free. There is an organization in Chicago called, “Free Tours By Foot” that offers free tours of different areas of Chicago, giving you a history lesson along the way. They don’t ask for anything, other than donations if you enjoyed their tour, and you decide how much.
Other fun and mostly free things to do in Chicago include the Air & Water Show that runs in August, and if you happen to be planning a vacation in July, you’re taste buds are in luck. That’s when the “Taste Of Chicago” occurs. Area restaurants offer special prices for special tasting portions, and should easily offset the costs of that afternoon cocktail overlooking the waters.
From June through September you can enjoy free music festivals in Chicago’s parks, with the like of the Blues Festival, Jazz Festival and World Music Festival to enjoy.
A major concern in a major city on vacation is always food, because you can certainly spend a bunch of cash on it. Visiting Chicago, there are two meals that this town is famous for, Deep-Dish Chicago Style Pizza, and the Chicago-Style Hot Dog, both guaranteed not to empty the wallet.
Keeping Cool in Chicago on your summer vacation
If you don’t already have one of those pump spray bottles with built in fan, get one and fill it with ice cubes. Mist yourself every once in a while and you’ll be surprised how much cooler you will feel. And, if you don’t have one with a fan, just get one that sprays, because even that will help cool you off.
Another cooling lifesaver is the standard, or exotic bandana that can be soaked in cold water, or filled with ice cubes. Stick it around your neck, apply it to wrists and armpits (only if you dare), and keep cool.
Always pack a bathing suit whenever you travel, especially during summer months. These days its rare to stay in a hotel that doesn’t have a swimming pool, especially in the Windy City. Take advantage of it if you can, because cool is in, especially in heat of summer.
Now lets look at things you can do in Chicago and still stay cool. For one, it’s a given that most people enjoy shopping, and admit it mister, there’s always a store or two in malls just for guys. These shopping experiences thrive on bringing in shoppers, especially during the summer, that’s why their air conditioning systems are so good. Take advantage and plan a few hours midday in one of the shopping malls, where you can have lunch and maybe even check out a movie in the theater.
Now if you’re careful, a day at one of Chicago’s beaches can be a great experience, especially swimming in the lake. With 26 miles of waterfront including 33 beaches, get there early enough, bring towels and check out a beach umbrella to stay out of the sun.
The most popular beaches are 63rd Street Beach, Montrose Beach, Loyola Park, North Ave Beach and Oak Street Beach.
The Montrose Beach is the one you want if you brought along Fido, because it’s a Dog Beach and your pup is welcome.
If you are looking for a beach experience with a party attitude, then downtown in the Lincoln Park area is North Ave Beach. Here is where you find the party crowd at the Castaways Bar. Just remember, drinking cold alcohol beverages really doesn’t cool you off, they just make you forget how hot you are.
We hope this article and its suggestions will help keep you and your family healthy and safe on your Chicago Vacation this year.
Going Cheap in Chicago
I should preface that with a friendly reminder that you do have to be a fan of walking and a couple of miles of moving along on your feet has to be what you consider fun. If this describes you, it is easy to have a fun and inexpensive time in this very impressive town.
Before we start, you will need to find a hotel in the Downtown area, sure public transportation can get you around, but if you aim to use your feet you will have to seek out good lodging deals in the Downtown area. They do exist and depending on the season they can easily beat out comparable hotels in big cities across the country.
Next, utilize public transportation, even though most of the attractions that you want to see may be close by there are a few spots that are best seen via train or bus. Grab a 1, 3 or 5 day rail pass and you’ll save money on getting around. The train is faster but the bus allows you to see more of the city. (Note: the bus tends to crawl around during high traffic times, so be aware of scheduling conflicts and allow for extra time if you utilize the bus).
Navigating the city is very simple, just remember that Michigan Avenue is where you’ll do most of your sightseeing as your trip starts. (it runs north to south) You will branch out, but getting the lay of the land is simple once you understand that a river crosses Michigan Ave. (Chicago River) and heads east toward Lake Michigan. Grant Park is between Michigan and the Lake. Simple, right? Keep heading north and you’ll get to Oak Street Beach. If you head south you’ll get to Hyde Park and the University of Chicago as well as the neighborhood that President Barack Obama calls home.
Things you should see that are cheap in Chicago:
• Oak Street Beach – Yes, I am telling you to go and see a beach in a city that is so dynamic and interesting. The views from this side of town are spectacular and you’ll realize it the minute you frame a shot with Lake Michigan on the left and the city on the right. (Hint: It seems like city views are spectacular from so many points of interest in Chicago)
• Lincoln Park Zoo (Free) : One of the oldest zoos in the US. Typically crowded on the weekends, but a really peaceful and immersive treat during the weekdays. My favorite thing to do is go to the McCormick Bird House during the birds’ feeding and watch the tentative interaction between the zookeeper and the pair of Blyth’s Hornbills (the zookeeper uses a clicker to distract the hornbills and throws a few grapes in its beaks before quickly plopping down the bowl of food). Also, when they flap their wings, it sounds like thunder—very loud and disarming.
• Lincoln Park Conservatory (Free) (Next to the Lincoln Park Zoo): A stunning sea glass-colored structure that houses a verdant fern room. Make a game out of finding the semi-hidden dinosaur figurines.
• Free Concerts in Orchestra Hall at Symphony Center (Free): Concerts are not given by the CSO, but by the Civic Orchestra. There are typically 6 concerts per season. There’s a preconcert lecture as well for folks who want to learn more about the evening’s performance.
• Graceland Cemetery (Free): Self-guided walking tour is available at the visitor’s center. Beautiful Victorian-era cemetery/park that’s well-maintained. All the architectural greats and business magnates are buried here: Mies Van Der Rohe, Louis Sullivan, Daniel Burnham, Marshall Fields, George Pullman, etc. Personally, I would recommend going on a walking tour guided by a Chicago Architecture Foundation docent to maximize you time. You have to leave before 4pm, though, or risk getting locked in for the night!
• Chicago Architecture Foundation Walking Tours (starts at $15): So many great walking tours that last about 2 hours. I would recommend any of the walking tours that take place in the Loop (e.g., “Downtown Deco” or the “Daniel Burnham: Architect, Planner, Leader” tours) which provides the most shot-to-the heart stunning view of Chicago’s strong architectural heritage.
• Maxwell Street Market (free): One of the oldest street/flea markets in Chicago. Known for their vibrant Mexican food vendors. One of Rick Bayless’s favorite places to grab a meal.
• Free Museum Days: Pretty self-explanatory. The line for the Shedd Aquarium is always the longest and free is always good.