Whether you’re a native or a newbie, Chicago tours offer a way to see a part of the city you might not have seen before. From food tours to walking trips for little feet, we’ve got a great list to get you started exploring this great urban landscape. Plus, we designed plenty of our own, customized (and FREE) tours to explore the city and suburbs.
Whether you’ve lived here all your life, or are new to town, we’ve got a tour that will show you a different side of Chicago for families.
If you’re ready to experience a little downtown nightlife withthe kids without the hassle of driving yourself, try hopping on adouble-decker bus or trolley for a tour of the city’s lights. Forthe first time, the iconic red buses and green and red trolleyswill traverse the city after dark during the summer months.
If you’re ready to experience a little downtown nightlife withthe kids without the hassle of driving yourself, try hopping on adouble-decker bus or trolley for a tour of the city’s lights. Forthe first time, the iconic red buses and green and red trolleyswill traverse the city after dark during the summer months.
The hour-long tour includes four hop-on, hop-off points andfocuses on Chicago’s well-known architecture and hot spots likeMichigan Avenue and the lakefront. The nighttime tour comes after asuccessful holiday lights tour season.
“We found that in doing the holiday lights Â… Chicago has iconicbuildings that take on a different look and feel at night, forinstance Buckingham Fountain, the Wrigley Building and Water TowerPlace,” says Rob Pierson, president of Chicago Trolley.
The evening tour starts at 6 p.m. and lasts until 11 p.m., soriders can hop off, visit downtown and then hop back on. The tourencompasses the John Hancock, North Michigan Avenue, portions ofLake Shore Drive, Millennium Park and much of the downtownarea.
Passengers who buy the daytime Signature or Neighborhood trolleytour tickets can ride the evening trolley for no additional charge,Pierson says.
The tour is partially narrated, but also includes plenty ofquiet time to just sit back and enjoy the scenery.
The evening tours are appropriate for all ages, Pierson says,and will appeal to even the most seasoned Chicago residents.
“How often are they in the downtown market in the evening, in anopen-topped vehicle, where they can sit out in the fresh eveningair with a 360 degree view of the skyline?” Pierson asks. “It hasan attraction for both in-towners and out-of-towners.”
There’s a whole fascinating, climate-controlled worldunderground in Chicago’s pedways. This tour will take you below thecity.
The Chase Bank building downtown might seem to be just anotherglass-faced skyscraper in the ranks of the Loop. But when you’relooking at it with Chicago Detours, all of that changes.
Having lived in Italy as a tour guide and worked as a researcherfor Rick Steves’ travel guides, Detours founder Amanda Scotesecreated cultural tours because she realized people were missing outon great history in their own city here at home.
On our Inside the Loop: Expect the Unexpected tour, we woundthrough various buildings in the Loop and into the undergroundPedway. I was amazed at all the things I’d never noticedbefore.
As we walk, Scotese points out older buildings, a courtyardhidden from street level, and small spaces nestled beside gleaminggiants, drawing out observations and opinions from both adults andchildren.
Four adults in our group hold iPads and open up photos andvideos at different points in the tour.
“We build the tour by digging through archives and newspapers,old stories and photos,” Scotese says. “And then we use the mediato help bridge the gap in time to connect with the past.”
There are three young people in our group: my 12-year-old son, ayounger boy and a teenager. All of them listen as intently as theadults and participate in the group discussions.
My son was fascinated by the curve in a modern building’sarchitecture that gives the illusion he could run right up the walland he joined in a lively discussion about the Picasso in DaleyPlaza.
This is really the sort of experience that depends on the kid-ifyou have a history buff, they are sure to have fun. But evenrestless kids will get a good walk in during the two-hour tour andpick up some fascinating Chicago history on the way.
We ended beneath the dazzling dome of the Chicago CulturalCenter. Walking almost reverently through the gleaming space, wetook photos and watched the sun setting over Millennium Park.
My husband, son and I all agreed that this was a great way tospend a Sunday afternoon together. My son can’t wait to try out hiscomplimentary map of the Pedway routes in the Loop and we’realready planning our next tour.
Chicago Detours offers both public tours and private group tours.For information on public tours, visit chicagodetours.com or call(312) 350-1131. For information on private group tours, email privatetours@chicagodetours.com.
Use this scavenger hunt created just for families by ChicagoParent to explore downtown Chicago.
Take a treasure hunt in the city
Everyone loves to find treasure, whether it is a bit of seaglass on the beach or an Ann Taylor sweater from the Goodwill rack.Letterboxing, a new trend in treasure hunts, lets families follow atrail of clues to discover hidden gems throughout the city andsuburbs.
Getting started is easy. All that is required is the purchase ofa stamp, ink pad, pen and log book. It is also nice to have acompass, as some of the clues use directional bearings. Next,download clues from one of the websites (atlasquest.org or letterboxing.org) and start
boxing.
The person who finds a box stamps the log book inside with theirpersonal stamp, and then stamps their own log book with the stampfrom the box. A pen is used to record the date and sign your trailname. Part of the fun of letterboxing is coming up with your ownunique nom de plume with which you sign in. You may find yourselfin the company of Waltzing Pigs, Atomic Beans, Chicken and Stars,Frog Man or Fly Girl.
Typical hiding places for letterboxes can include forestpreserves, parks and cemeteries. Occasionally they are even plantedin a public business, where access to the box is obtained byrepeating a code word to an employee, such as the one I found in alocal ice cream parlor.
“I would like an extra large eggplant avocado trough please,” Isaid to the woman at the counter, repeating the secret words.
With a smile the waitress reached under the counter and broughtout a square plastic box.
“Sure thing. Here ya go.”
Relieved, I sat down at a table and stamped in beforeconsidering the ice cream flavors on the menu.
A pre-made stamp is fine for beginners, though most seriousletterboxers create and carve their own one-of-a-kind stamp. TheSpeedball Speedy-Carve Basic Stamp Making Kit from Amazon includesdetailed instructions and all the materials needed for a firstattempt.
The best way to get to know the real Chicago is using
your stomach. Join a Chicago pizza tour and decide for yourself who
makes the best in the city.
A bite of Chicago’s pizza scene
We all know Chicago is the home of deep-dish pizza, but there isso much more to the story. After Cubs versus Sox, Uno’s versusMalnati’s must be the second biggest local rivalry.
Recently, I joined a pizza tour to get the inside scoop onChicago’s pizza scene and sample the different ways cheese,tomatoes and bread can be compiled.
Slice of Chicago Pizza Tours offers a two-hour walking tour thatcovers one mile and gets you three slices of pie while feeding yourmind with pizza lore and fun facts-Did you know people in Americaeat 350 slices of pizza per second?
Our guide traced the history of pizza in Chicago from its humblebeginnings in the wooden bathtubs of Taylor Street in Little Italyto its explosion after World War II, which led to the opening ofPizzeria Uno in 1943.
The tour starts at Pizzeria Uno, 26 E. Ohio, although it doesn’tgo inside the restaurant. With a seating capacity of 100, thehistoric institution prefers to bring out paper plates of pipinghot slices to eat while standing on the sidewalk. To make thiseasier for the kids, bring a bottle of water and some wetwipes.
From the granddaddy of Chicago pizza, we walked to a relativeunknown on the pizza scene, Pizzeria Ora, and were quickly seated.The walk also stops at Giordano’s and winds past other pizzalandmarks.
This tour is great for tweens on up, especially growing boys.Besides a big stomach, our tour guide, Will, recommends that aninterest in history helps.
And the three mini-slices really do fill you up. Even the pairof 15-year-olds on my tour agreed at the end they couldn’t eatanother bite.
Mostly crammed along a six-block stretch of Wentworth Avenuenorth and south of Cermak, Chinatown is a hodgepodge of gift shops,restaurants, grocery stores and candy shops. Navigating withsmall children takes a little extra planning. Strollers, forexample, are difficult. And you may want to limit your jaunt to afew blocks, rather than the full stretch. Here are some helpfulhow-to’s.
Chinatown for little feet: A guided tour
The jumble of old and new, bold and subdued,treasure and trinkets that is Chicago’s Chinatown has fascinated mesince my parents started toting me there for Sunday lunches when Iwas little. Decades later with my own kids in tow, there’s stillthe same untamed, what’ll-I-find-today, street-bazaar feel thatensures no two trips will be alike. Mostly crammed along asix-block stretch of Wentworth Avenue north and south of Cermak,Chinatown is a hodgepodge of gift shops, restaurants, grocerystores and candy shops.
Navigating with small children takes a little extraplanning. Strollers, for example, are difficult. And you may wantto limit your jaunt to a few blocks, rather than the full stretch.Here are some helpful how-tos:
Start in the middle
Parking in the big Chinatown lots just north of the cornerof Wentworth and Cermak puts you smack in the middle of thedistrict’s two main shopping areas. For a more kid-size trip,choose one side or the other. Either way, if you have astroller-age child, this is one outing where you’ll do better witha backpack-style kid carrier-much easier to navigate the crampedquarters and ins-and-outs of the many small shops.
But if stroller you must, you’ll be better off headingnorth where you can walk Chinatown Square and head along thetree-lined pedestrian-only, two-level mall of shops.
View, eat, shop
Each family will have its own Chinatown rhythm andpriorities, but with kids along, it’s helpful to let everybody knowthe basic game plan before you set out.
For us, it’s worked well to let our kids know they’ll eachhave the opportunity to buy one inexpensive gift store item beforewe leave. To keep them from clamoring for that purchase throughoutthe entire trip, we say we won’t buy any trinkets until afterlunch. This way, the kids have more fun window shopping during ourwalk and are more likely to look at a wider array of items beforemaking their final decision.
Photo Slideshow
Then we have our snack or lunch break at one of therestaurants or bakery/tea shops. We retrace our steps to buy eachchild’s chosen trinkets on the way back to the car. Be forewarned:There are a lot of gift stores full of inexpensive, brightlycolored swords, dolls, tea sets and other toys.
This is not Disney
Much of what you’ll view in Chinatown may be unfamiliarand exotic. Think tea-smoked ducks, hanging by their necks on hooksin windows with other barbecued items, such as powerfully odiferousdried fish and oddly twisting ginseng, herbs and mustymedicinals.
This is a great place for your kids to experiencesomething new and different with you to guide the way. Beadventurous! If you are willing to taste or smell something youhaven’t tried before, your kids will follow yourexample.
Northerly stroll
Walking north and one block west of the Chinatown parkinglot along Archer Street puts you at Chinatown Square with its mallof shops and restaurants. There are lots of shade-producing ginkgotrees and seating areas along the pedestrian-only avenue rightthrough the middle.
Things to see here: Look to the trees around the squarefor decorative red lanterns hanging among the branches. Check outthe stone and metal sculptures of the 12 animals of myth and legendfrom the Chinese Zodiac.
Start in the city, but westward ho! on the train to visithistoric villages and a great children’s museum. This is ado-it-yourself tour to get you started exploring the western suburbof Naperville.
Train-tripping: Westward, ho! to Naperville and Lisle
There’s just something about train travel:The impressive size of the towering silver cars. The niftyflippable seats, upper deck, green-tinged windows, squeal of metalagainst metal and the big Chicago ticket takers punching ticketsand bantering with the boys.
My kids still get their electrono-gadgets out, but focuson them less, mesmerized as they are by the long, thin ribbons oftrack, sway of cars and the backside view of the guts and alleywaysthat butt up against railways. Our train-trippingadventures are all about that: making the journey part of theadventure.
Our pick for fall: A Metra-train journey on the BNSF line toNaperville and Lisle. The trip is scalable: All-day, if you includestops at the DuPage Children’s Museum, Naper Settlement and Museumat Lisle Station Park. Shorter, if you cut one or two of thosedestinations out.
The route Start at Union
Station, 225 South Canal St., that monolithic Chicago hulk of a
commuter hub, which is itself fascinating to kids. Catch the BNSF
train to Aurora, getting off at Naperville.
The cost It’s $5 each way
for an adult train ticket; $7 for unlimited weekend rides.
Weekdays, kids 7-11 are 50 percent off; kids under 7 ride free.
Weekends kids up to 11 ride free with an adult. Admission at the
DuPage Children’s Museum is $8.50 per person. Naper Settlement
entry fees are $9 for adults, $6.50 for kids. The Museum at Lisle
Station Park is free.
Tips Start early! Leaving on
the 7:45 a.m. train will put you at the children’s museum just as
it opens at 9 a.m. (Museum hours are 9 a.m.-4 p.m. Monday-Friday, 9
a.m.-5 p.m. Saturday, noon to 5 p.m. Sunday). Pack water,
sunscreen, snacks and books or toys for the journey.
Suggested day plan
7:30 a.m. Arrive at Union
Station and buy round-trip tickets to Naperville.
7:35 a.m. Board
train
8:45 a.m. Arrive at the
Naperville train station. From here, take the stairs and ramp that
will bring you under the tracks and up across the street to DuPage
Children’s Museum, 301 N. Washington St. Geared for kids birth-10
years, there’s lots to keep children interested. Long-standing
favorite exhibits include the Waterways water play area and
AirWorks drying tunnel and blowers and the Build It construction
area. On Sept. 14, the museum launches a new exhibit upstairs, “The
Play’s the Thing,” featuring a stage and props for budding set
designers, costumes and special programming including plays,
puppets and dramatics.
11 a.m. It’s about a 15
minute stroll south on Washington and west on Aurora Avenue to get
to the Naper Settlement. (Note: We like tucking an extra 15 minutes
into the journey, allowing us to meander west along Naperville’s
Riverwalk (covered bridges, ducks, fountains and flowers) before
crossing over to the settlement at 523 S. Webster St.). Naper
Settlement is an outdoor history museum depicting an old-time
19th-century Midwest village. Enter the settlement through the
Pre-Emption House Visitor Center, Naperville’s oldest hotel and
tavern. From here, you can ramble along the settlement’s streets
viewing blacksmiths, stonecarvers and printers at work. Costumed
volunteers roam the 12 acres of grounds and 30 buildings, bringing
the scene to life. There are log homes and mansions, churches and
shops, plus, an 1840 schoolhouse still scratched with kids’
graffiti that’s centuries old.
1 p.m. At this juncture,
you’ll need to decide if you want to head home or continue on to
Lisle. Either way, you’ll be ready for lunch. Walking back to the
train, there are nume
Pack some kid essentials, spring for a CTA pass and visit theseChicago el destinations on this do-it-yourself tour. We’ve createda step-by-step guide to make the day easy!
Train-tripping: Brown and Red Line trips for little feet
El trains and neighborhood dining: Knowing your way around bothis the mark of a true Chicagoan. No matter how deeply you’ve divedinto dining-by-district or traveling-by-train, we figured you’denjoy taking the kids along for an introductory ride that combinesboth.
We’ve planned two, kid-sized progressive-dining adventures withjust a few stops at restaurants and neighborhoods easily reachedfrom the North Side Red Line and Brown Line.
What you’ll need: Plenty of cash for restaurant sampling (whatyou can’t eat you can carry out), good walking shoes and a coupleof disposable cameras.
These trips can be done with a stroller, but are better-gearedto parents with kids 5 and up. You’ll need a $5.75 unlimited daypass for each adult, $1 for kids 7-11, free kids 6 and under, whichlet you hop on and off the train at each dining hub. We’ve plannedeach trip around el stops with elevators/escalators. Travelingbetween 9:30 a.m. and 2 p.m. should mean trains are less crowded.Expect to wait from 10-15 minutes for trains.
Wend your way through the German/continental food offeringsaround Lincoln Square, down some Southen grub at Wishbone, thenback via the Brown Line.
Western stop
Park in one of the metered lots. Before you board, start withsomething light from Cafe Selmarie, 4729 N. Lincoln (Selmariegranola with yogurt and fruit, $6; fresh baked brioche, $1.95, ormaybe a breakfast pastry to share), next to the fountain inGidding’s Plaza. Explore some of the shops (Quake Collectibles,4628 N. Lincoln, a used-toy store with more action figures than youcan imagine, is a huge motivator for my sons’ good deeds). Don’tmiss the house-made sausages, European cheese and shelves full ofmarzipan at Gene’s Sausage Shop, 4750 N. Lincoln. Now hop the traindown through Ravenswood to the Montrose stop.
Montrose Avenue stop
By now, you’ll be ready to grab a coffee. There’s Beans &Bagels, 1812 W. Montrose, for the independent-java-minded(Metropolis coffee) and a Starbucks. Ogle the menus and marquee atMargie’s Candies, 1813 W. Montrose, a neon-bedecked little placefor old-fashioned ice cream sundaes. (If the kids are good, maybestop here on the way back.) Travel to Paulina.
Paulina stop
Walk two blocks south to Wishbone. In the late ’80s, the Nicksonbrothers-each some combination of writer, artist, chef,filmmaker-took Chicago by storm. One brother, Joel, launched alittle breakfast place on Grand Avenue that became so popular, ithatched three more restaurants. Twenty years later, Wishbone’s 3300N. Lincoln location is one the family-friendliest of the ‘bones.Introduce your kids to honest, approachable Southern fare minus theBubba kitsch. The great kids’ menu is full of easy-access items(cornflake crunchy french toast, one-eyed-Susan sunny-side-up eggin toast, etc.). You’ll be ready to walk the few blocks back to thePaulina stop to head home.
The richly varied layers of Chicago’s ethnic diningpossibilities fill city foodie Web sites with questions, tips,rants and raves around the clock. Where to start … How about theRed Line? From Caribbean-baked treats just east of the HowardStreet stop, down to a panoply of Southeast Asian options west ofthe Argyle stop, this teeny food tour will let you and your kidssample plenty of flavors. As I tell my 10-year-old when his eyesglaze over with too many menu options: “Just pick something-if youdon’t like it, don’t worry: you’ll eat again.”
Howard Street el stop:Caribbean
Park your car in the ample lots here. Before you get on thetrain, walk 1½ blocks east o
Planning day trips for the under-4 set means scaling things downto tot-sized capabilities. Thinking a little smaller will boostyour enjoyment of the day, empower your little one and, ultimately,help you step out more often. These three pint-sized outingsstart from the same Lincoln Park Zoo parking lot hub and are timedto end before momentous meltdowns ensue.
Lincoln Park Zoo in Chicago: a guide for families with young kids
Planning day trips for the under-4 set means scaling things downto tot-sized capabilities. Thinking a little smaller will boostyour enjoyment of the day, empower your little one and, ultimately,help you step out more often.
These three pint-sized outings start from the same LincolnPark Zoo parking lot hub and are timed to end before momentousmeltdowns ensue.
The lakeshore section of Lincoln Park is one of Chicago’sbest spots for short, cheap trips, all doable in less than aday.
How far can you expect a 3-year-old to walk? “It varieswith each child,” says pediatrician Dr. Lisa Thornton, “but even afew blocks is on the outside limit.” Travel light with one sturdybackpack, but be sure to include:
- Some cash. Both the zoo’s carousel and train are $2.75 aride, cash only (standing adults have to pay, too).
- Lots of water. Try to get kids to sip some water (notjuice) every 10 minutes or so.
- A stroller, sturdy kid carrier or wagon. Encourage kidsunder 3 to walk some, but expect to carry or give rides,too.
- Sunscreen/hats/sunglasses.
- Snacks. Feed little ones some yogurt and carbs before youstart-avoid sugar at this point. Take a snack every half hour orso-fruit and peanut-free trail mix is good. After the trip, you canhave that cookie.
- Potty breaks. Expect little ones to have to relieve theirbladders at least once an hour.
Click one of the three tours below to getstarted!
Behind the scenes at Soldier Field
It’s that time of year again. The time when we put aside ourNorth and South side allegiances and come together to support thoseMonsters of the Midway, the Chicago Bears.
Football fanatic families-and you know who you are-shouldconsider taking one of Soldier Field’s stadium tours. They’re achance to get into the historic stadium for a fraction of whatyou’d spend on game day and to explore some typically inaccessiblespots.
The stadium itself is a fascinating place: a futuristic”spaceship” plopped onto some ancient-looking Roman columns. You’llpick up some interesting trivia related to the stadium’s nearly100-year history and its renovation in 2001. And in honor of thestadium’s name, you’ll get the chance to see some medals thatbelonged to those who have served and the famous Doughboy Statuethat used to be in Garfield Park.
A trip up to the Colonnades-those imposing columns seenfrom afar-is a lesson in architecture and gives some great views ofthe city.
But the real thrill comes from walking in the footsteps offootball greats, from George Halas to Walter Payton to DevinHester. The kids on my tour couldn’t suppress their awe at standingon the sidelines of the field. And although the Bears’ locker roomis off-limits, you still get to see where some pretty famousfootball players have suited up (or mourned a loss) in thevisitors’ locker room.
I also enjoyed getting to see how the other half liveswith a brief stop in the Skyline Suite, an expansive box that givesa bird’s-eye view of the field (and costs $900).
Although my tour was populated by plenty of people wearingblue and orange, you don’t have to be a diehard to enjoy theexperience. And since it’s less than an hour long, even young kidswon’t be too bored.
I’d recommend taking advantage of the beautifulsurroundings and spending the day (also better bang for your buck,parking-wise) in the area. Soldier Field is in the middle of alovely park and next to some of the world’s finest museums. Youcould even bring along a pigskin and have a toss.
What better way to celebrate fall’s favoritegame?
