Your Kind of Town
Positioned proudly in the middle of the country, Chicago is a vibrant, welcoming city that bursts with world-class museums, ethnic neighborhoods, a stunning skyline and a system of parks that string along the city’s lakefront like a jeweled green necklace.
Indeed, all the land along the city’s lakefront is devoted to public parkland. It is one of Chicago’s biggest assets, giving the city an openness and natural beauty. An 18-mile paved running path hugs the Michigan shore, populated by joggers, power walkers and baby strollers. The stunning Millennium Park, with its iconic, highly polishepd “Bean” statue that reflects the downtown skyline, abuts the Art Institute of Chicago, where galleries are filled with notable pieces by the great masters.
The Great Chicago Fire of 1871 set the town ablaze but misfortune turned into good fortune, as the city was completely rebuilt. City developers were able to start anew, planning the widespread parklands and a grid system for streets that makes the city easy to navigate. Old shacks were cleared out and in their place rose Art Deco skyscrapers and, later, soaring modern office towers.
Yes, it can get cold here in winter—Chicagoans bundle up and hunker down when icy winds blow in January and February. (Fun fact: Chicago is called the Windy City due to its blustery politics, not its weather). But spring, summer and fall bring excellent weather for exploring museums, shopping on Michigan Avenue, enjoying street fests and eating in restaurants of every stripe.
Chicago is a city of immigrants and neighborhoods, resulting in a true melting pot of restaurants, with a range that runs from small ethnic spots to hip eateries helmed by celebrity chefs. Residents are friendly here—quickly chiming in with their favorite places to eat and visit. Gluten-free and allergy-free options grow by the day, with many restaurants offering gluten-free menus and happily accommodating diners on special diets. Still, when dining out in any city, always talk to a manager to assess their attention to special diets. In general, avoid busy times and always make sure you feel comfortable that the staff will give your special meal the attention it needs.
We’ve put together a suggested sightseeing and dining itinerary, focused around popular attractions. There’s a lot packed into each day. Don’t expect to do it all; feel free to pick and choose to craft a tour that works for you. For more sites and events, visit explorechicago.org, the city of Chicago’s tourism site.
There are hundreds of hotels in the Chicago area. Downtown lodging can book up quickly during popular summer months and during big conventions that draw thousands to the city. Business travelers head to hotels in the Loop, close to many businesses. Leisure travelers will want to stay near North Michigan Avenue, the prime shopping and dining destination. Here are two well-regarded hotels in good locations. For others, check tripadvisor.com.
The Peninsula Chicago (108 E. Superior St., 312-337-2888, 866-288-8889, peninsula.com) is an elegant luxury hotel in an ideal location, just off Michigan Avenue. Exquisitely furnished, the hotel has top-notch service and accommodations. The Peninsula’s attention to detail and its emphasis on wellness extend to The Lobby restaurant, which offers vegan and gluten-free menus. For a true treat, try the elegant gluten-free or vegan afternoon tea service.
On a smaller scale, Hotel Palomar Chicago (505 N. State St., 312-755-9703, 877-731-0505, hotelpalomar-chicago.com) is a Kimpton Group boutique hotel with rooms that are comfortable and chic. Located in River North, just a couple of blocks north of the Chicago River and west of Michigan Avenue, the Palomar is close to many popular restaurants and nightlife options. The onsite restaurant, Sable Kitchen & Bar, accommodates guests by offering gluten-free options.
Both hotels are just a few blocks from Whole Foods Market (30 W. Huron St., 312-932-9600) and Trader Joe’s (44 E. Ontario St., 312-951-6369), where travelers can stock up on allergy-friendly cereal, snacks and sandwich fixings for inexpensive breakfast in their hotel room or to pack lunch to go for the kids.
Start your tour at the Chicago Cultural Center (77 E. Randolph St., 312-744-6630, explorechicago.org), which was once the main site of the Chicago Public Library. Inside the Randolph Street entrance, the Visitor Information Center has maps, brochures and free Chicago Greeter tours to get you started. Head upstairs to Preston Bradley Hall to see the world’s largest stained glass Tiffany dome.
To help appreciate Chicago’s spectacular skyline, the Chicago Architecture Foundation (224 S. Michigan Ave., 312-922-3432, architecture.org) hosts many interesting tours of the city, including a popular architectural river cruise. Put on your walking shoes for the “Historic Downtown—Rise of the Skyscraper” tour, a two-hour walking tour that highlights early skyscrapers.
Across the street from the architecture foundation is the Art Institute of Chicago (111 S. Michigan Ave., 312-443-3600, artic.edu/aic), which has a fabulous collection of famous paintings. Head to the second-floor Impressionist and Post-Impressionist galleries to see artwork by Seurat, Renoir, Monet and more. The new Modern Wing is a stunning addition to the museum, with not-to-be-missed modern and contemporary art from Picasso to the present.
Enjoy great views of the city’s skyline as you cross the pedestrian bridge from the top of the Modern Wing to Millennium Park. Have lunch at Park Grill (11 N. Michigan Ave., 312-521-PARK, parkgrillchicago.com), which accommodates gluten-free diners with its contemporary American menu.
Parks dot Chicago, due to the city’s long history of support for public space, greenery and outdoor sculpture. The crown in the city’s park system is Millennium Park, just off Michigan Avenue between Randolph Street to the north and Monroe Street to the south. In Millennium Park, the highly polished stainless steel Cloud Gate sculpture, nicknamed “The Bean” with its shiny metallic finish, reflects the city’s stunning architecture above and tourists below. The Frank Gehry-designed Jay Pritzker Pavilion hosts many free outdoor concerts in summer. Check millenniumpark.org for a list of events. Stroll south along the promenade to the Crown Fountain, two towers that display changing electronic pictures of faces of Chicago’s citizens. Pack swimsuits for the kids—in summer, the faces spit out sprays of water to the delight of children who splash below.
After 5:00 pm is a great time to see twinkling night views from the Skydeck (233 S. Wacker Dr., 312-875-9447, theskydeck.com) at the Willis Tower (formerly the Sears Tower), the tallest building in the city. The 103rd floor Skydeck has a stellar vista of the city—actually a span of up to four states—as well as a breathtaking view from The Ledge, a glass balcony that extends in midair, 1,353 feet above the ground.
For dinner, hit Hub 51 (51 W. Hubbard St., 312-828-0051, hub51chicago.com), part of the Lettuce Entertain You (leye.com) restaurant empire. Almost all Lettuce restaurants have gluten-free menus and staff trained to accommodate food allergies and gluten-free requests. Hub 51 offers an eclectic gluten-free menu, from sushi to pulled chicken tacos.
North Michigan Avenue
Spend the day shopping and sightseeing. Fuel up with breakfast at Feast (25 E. Delaware Place, 312-337-4001, feastrestaurant.com), which has a gluten-free menu of comfort foods and breakfast favorites. Take an early morning walk along nearby Oak Street Beach (Lake Shore Drive and Oak Street). Its sandy shore attracts sunbathers and volleyball players who flock to the water’s edge.
If you didn’t make it to the Willis Tower on Day 1, you’ll get an equally good view of the city at the John Hancock Observatory (875 N. Michigan Ave., 888-875-VIEW, jhochicago.com) on the 94th floor of the John Hancock Tower. Just down the street, the Museum of Contemporary Art (220 E. Chicago Ave., 312-280-2660, mcachicago.org) hosts compelling exhibits and provocative performances.
The stretch of Michigan Avenue from Oak Street to the Chicago River is called the Magnificent Mile (themagnificentmile.com), famous for its blocks of ritzy shops. You can shop till you drop at department stores and popular retailers. On Oak Street, you’ll find even more tony high-end boutiques.
Water Tower Place was one of the first vertical malls in the United States, with 100 stores. For girls–especially gluten-free girls—the highlight is American Girl Place (835 N. Michigan Ave., 877-247-5223, americangirl.com). In addition to being a fantasyland for girls to shop, American Girl Place is a dining dream for families on special diets. A gluten-free menu and allergy-friendly options at breakfast, lunch and dinner ensure that your little princess is treated just as royally as the rest of your family. You must make reservations several weeks in advance. (If you don’t have reservations, show up at one of the seating times and ask if there are any cancelations.)
Also in Water Tower Place, Foodlife (835 N. Michigan Ave., 312-335-3663, foodlifechicago.com), a contemporary food-court concept, has gluten-free options.
During summer, boat cruises on Lake Michigan and the Chicago River are a great way to enjoy the sun and find out more about the city’s striking architecture and history. The Chicago Architecture Foundation has a popular architecture river cruise aboard the Chicago’s First Lady (book online at cruisechicago.com or call Ticketmaster at 800-982-2787), as does the Chicago History Museum, which offers its architecture and history boat tours through Chicago Line (312-527-1977, chicagoline.com).
Tourists, especially families with kids, flock to Navy Pier (600 E. Grand Ave., 312-595-PIER, navypier.com), a former naval pier turned entertainment center. The giant 150-foot Ferris wheel gives you breathtaking views of the lake and skyline. (Fun fact: the Ferris wheel was invented in Chicago for the World’s Fair of 1893.) The Chicago Children’s Museum (700 E. Grand Ave., 312-527-1000, chicagochildrensmuseum.org) makes its home on Navy Pier, as do dozens of stores and kiosks selling souvenirs galore.
Off the Pier, River North offers several dining options for special diets. From the folks who invented the Weber kettle grill, the Weber Grill Restaurant (539 N. State St., 312-467-9696, webergrillrestaurant.com) serves steaks and kettleburgers with gluten-free buns.
Of course, Sweet Home Chicago is famous for the blues. For evening entertainment, check out a legendary Chicago blues club, like Buddy Guy’s Legends (700 S. Wabash Ave., 312-427-1190, buddyguy.com) downtown, or Kingston Mines (2548 N. Halsted St., 773-477-4647, kingstonmines.com) or B.L.U.E.S. (2519 N. Halsted St., 773-528-1012, chicagobluesbar.com) in Lincoln Park.
Spend most of your day at the Museum Campus, home to three world-class museums. Start at the Shedd Aquarium (1200 S. Lake Shore Drive, 312-939-2438, sheddaquarium.org), as it can get very crowded later in the day. The Aquarium is home to many interactive exhibits and the beautiful Oceanarium, which has a popular aquatic show with Pacific white-sided dolphins and beluga whales.
Next, head to the neighboring Field Museum (1400 S. Lake Shore Drive, 312-922-9410, fieldmuseum.org), a top-notch natural history museum with interesting, interactive exhibits sure to engage kids and adults alike. For lunch, pack a sandwich and eat it at the museum, or if you go to the Corner Bakery (312-588-1040, www.cornerbakerycafe.com) inside the Field Museum, ask the manager to see the Bakery’s allergen guide.
Explore space—the final frontier—at Adler Planetarium (1300 S. Lake Shore Drive, 312-922-7827, adlerplanetarium.org), which has sky shows as well as exhibits about the cosmos. The new, ultra-high-tech Deep Space Adventure show takes you aboard a starship’s observation deck with stunning graphics and special effects.
Downtown in the Loop, the Atwood Café (1 W. Washington St., 312-368-1900, atwoodcafe.com) serves contemporary versions of classic American cuisine in an historic Art Deco building. The staff easily accommodates gluten-free and other special-diet requests. Catch a play in the downtown theater district. Big-name touring productions are part of Broadway in Chicago (312-977-1700, broadwayinchicago.com), which stages shows in several grand theaters downtown. The Goodman Theatre (170 N. Dearborn St., 312-443-3800, www.goodmantheatre.org) is a standout Chicago theater with powerful performances.
Wake up with the animals at Lincoln Park Zoo (2200 N. Cannon Drive, 312-742-2000, lpzoo.org), the nation’s oldest free zoo. The zoo’s small size makes it easy to walk around, perfect for a summer stroll.
If you’re lucky enough to be at the zoo on Wednesday or Saturday, head a few blocks south to Green City Market (south end of Lincoln Park, 773-880-1266, greencitymarket.org), a fabulous farmer’s market offering sustainable and organic produce. Keep an eye out for the city’s top chefs who shop here for unusual organic veggies. Bring a blanket for a fun picnic lunch.
Just south of the zoo, the Chicago History Museum (1601 N. Clark St., 312-642-4600, chicagohistory.org) has well-designed exhibits about Chicago’s past and present. Kids can pretend they’re giant hot dogs and pile on all the fixings of a Chicago-style dog (“a garden on a bun”), while adults learn about the city’s fascinating history.
Several restaurants provide allergy-friendly options in Lincoln Park. Don’t miss the guacamole prepared tableside at Adobo Grill (1610 N. Wells St., 312-266-7999, adobogrill.com), a festive Mexican eatery with a gluten-free menu.
Next to Adobo Grill is Second City (1616 N. Wells St., 312-337-3992, secondcity.com), the legendary sketch comedy club that has forged many a career, from Gilda Radner to Tina Fey. Also in Lincoln Park, Steppenwolf Theatre (1650 N. Halsted St., 312-335-1650, www.steppenwolf.org) is known for its compelling, innovative plays.
Hyde Park, home to the University of Chicago some seven miles south of downtown, prizes itself for its diversity and its academic wonkiness. The neighborhood is now also known for its most famous resident: President Obama, whose family home (not open to the public) is on South Greenwood Avenue.
The Museum of Science and Industry (57th Street and Lake Shore Drive, 773-684-1414, msichicago.org) is located in the only major building left from the World’s Fair of 1893. The museum’s collection is so extensive that it would take days to see it all. For a short tour, hit highlights like Science Storms, You: the Experience, and the U-505, the only German submarine in the United States.
For lunch, pack a sandwich and eat it at the Museum of Science and Industry, or head to Medici on 57th (1327 E. 57th St., 773-667-7394, medici57.com), a favorite Hyde Park hangout. The Medici has compiled a book that lists the ingredients of all its dishes, highlighting major allergens. It does not have a separate gluten-free menu but does offer gluten-free bread.
Architecture buffs will appreciate touring the Robie House (5757 S. Woodlawn Ave., 312-994-4000, gowright.org), one of Frank Lloyd Wright’s most significant residential buildings and a masterpiece of the Prairie style. The DuSable Museum of African American History (740 E. 56th Place, 773-947-0600, dusablemuseum.org) has a rich and diverse collection, including an exhibit about Harold Washington, Chicago’s first African American mayor.