Chicago Travel Guide
Where to Stay, Eat, and Explore in Chicago
Make the most of your time in the Windy City, whether you’re here for the culture and design, the food scene, a family vacation, or a first-time visit.
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March 03, 2026
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Travelers seeking big-city culture served with warm Midwestern hospitality will find it all in Chicago. It has a lakefront that stretches 28 miles, more than 7,300 places to eat, eight major league sports teams, and upwards of 200 theaters.
Summer brings festivals and outdoor activities galore, while winter encourages you to wander through one of the many world-class museums or cozy up at a cocktail bar with live music.
Whatever the timing and inspiration for your trip, Chicago is ready to show you a good time. Jump down to explore our recommendations for:
3,*
12pm check-in, when available
Room upgrade upon arrival, when available1
$100 credit to use towards eligible charges2
Late check-out, when available
1Certain room categories are not eligible for upgrade.
2Eligible charges vary by property.
3The Hotel Collection requires a minimum two-night stay.
Chicago Athletic Association
A one-time members club that’s now a destination for discerning travelers, the Chicago Athletic Association is marked by touches like leather sofas, brass headboards, and Bluetooth speakers disguised as old-time radios. It’s right on Michigan Avenue, offering easy access to the downtown district, The Loop, where you’ll find both award-winning restaurants and casual cafes.
Where to Eat
An all-day café in Lincoln Park that’s a neighborhood favorite for house-made Middle Eastern-influenced pastries and rich coffee roasts by day and good wines and dishes like lamb burgers by night. Book on Resy.
This lively Mexican spot in Logan Square puts its own spin on authentic, regional fare, with results like “DIY fish tacos”: warm, hand-rolled tortillas filled with fried skate wing “ribs” in a savory salsa. Book on Resy.
Ever, the award-winning restaurant, exemplifies modern fine dining in Chicago. Its multi-course tasting menu features artfully plated New American cuisine served in an elegant, minimalist setting designed to heighten every sensory detail.
A daytime bakery and one of Chicago’s most sought-after dinner tasting menus, with 13 courses inspired by the Filipino food chef Tim Flores grew up eating. They might include pancit, a traditional stir-fried noodle or kinilaw, a marinated raw seafood dish. Book on Resy.
Head uptown to Yooyee for some of the most authentic and fiery Sichuan in Chicago, from chewy, hand-pulled noodles to wok-fried fish curry. No reservations.
Named in honor of the chef’s French-Canadian grandmother, this quaint restaurant serves up contemporary French cuisine in a homey space. (Note that it was temporarily closed as of early October 2025 because of a fire.)
Visit France by way of Fulton Market at this 1960s Parisian-inspired cocktail bar that pours classic cocktails (including an entire menu section dedicated to the martini) alongside small bites. No reservations.
What to Do
A 50,000-square-foot foodie paradise, Time Out Market is a one-stop destination for sampling some of the best fast-casual spots in the city, from pizza and tacos to dumplings and burgers.
Take a three-hour tour of Chicago’s pizza scene led by an award-winning food writer and sample four different styles of ‘za, including Chicago’s signature deep dish.
Slip on an apron and join a hands-on cooking class, ranging from novice to expert, all taught by local chefs.
Pick up fresh produce at this community-focused Lincoln Park farmers market that hosts events, workshops, and classes for kids and adults. Open from 7am to 1pm every Saturday through late November.
Locals know Randolph Street as a Restaurant Row, for good reason. Stroll this West Loop stretch between Halsted and Ogden Avenue to discover some of the city’s most notable tables.
Sable at Navy Pier, Curio Collection by Hilton
Located directly on the iconic pier, Sable at Navy Pier, Curio Collection by Hilton offers a family-friendly lakefront stay with easy access to Chicago’s top sights. Stylish rooms and suites feature floor-to-ceiling views of Lake Michigan and the city skyline, with suites adding roomy living areas and convenient kitchenettes. Parents can unwind with cocktails by the fire pits at the nation’s largest rooftop bar, Offshore, while kids have rides, games, and seasonal fireworks just steps away.
Where to Eat
This old-school Italian joint in West Lakeview is a crowd-pleaser for Northern Italian-leaning hearty pastas and chicken parm the whole family can share. Book on Resy.
Locals and tourists alike flock to this South Loop diner serving an all-day breakfast menu (try the “cheeeesy waffle”) in casual digs where kids are always welcome.
Give sassy kids a taste of their own medicine at this themed diner where talking back is part of the experience: the servers are intentionally rude (it’s all in good fun) and the menu is classic kid stuff (jumbo hot dogs, burgers, and the like).
Elevated takes on classic Italian fare in a family-friendly space with locations in Lincoln Park and Highland Park. The Lincoln Park location also offers a convenient pick-up window. Book on Resy.
You can’t take the family to Chicago without sampling deep dish pizza and Pequod’s heralds itself as having the best in town (locals seem to agree).
Handmade pastas (like the spicy-but-not-too-spicy-for-kids Bucatini Arrabiata) are the standouts at this chic but family-friendly Southern Italian restaurant in Southport Corridor, just a few miles north of the Loop. Book on Resy.
Treat the kids to a scoop (or five) at this famed ice cream parlor that’s been serving its signature cone of chocolate, strawberry, Palmer House, pistachio, and orange sherbet since 1926.
A Chicago icon for over 100 years, Margies is an old-fashioned candy shop/ice cream parlor where kids can have their pick of old-time treats like toffee made with real butter and sundaes served in gravy boats.
What to Do
Head to the North Side to visit this waterfront boardwalk packed with family-friendly restaurants, carnival rides, shops, and art installations.
Visit this natural history museum (one of the world’s largest) to tour kid-friendly exhibits and partake in limited-time events about dinosaurs, animals, and plant life.
The second-oldest zoo in the country hosts dynamic educational programming for all ages throughout the year and even has its own family zoo – the Pritzker Family Children’s Zoo – with hands-on learning activities.
Blow off some steam along this paved 18.5-mile-long path along Lake Michigan where families can walk, jog, bicycle, or skate while admiring the views.
Known for its ancient Greek-style exterior, this acclaimed aquarium is home to more than 32,000 aquatic animals and invites kids to join immersive experiences like exploring a mini submarine in the Polar Play Zone.
This beach along Lake Michigan in Lincoln Park is a family favorite for volleyball courts, jet ski and stand-up paddleboard rentals, and spots to grab casual bites and ice cream.
The Gwen, a Luxury Collection Hotel
Located in a historic building on Chicago’s Magnificent Mile, The Gwen, a Luxury Collection Hotel marries 1930s-era elegance with modern amenities. Named after acclaimed local sculptor Gwen Lux, whose works are featured on site, the hotel’s suites deliver Art Deco charm and sweeping city views. For a crash course in the building’s heritage and Prohibition-era Chicago, head to the lobby at 2pm for the daily Epicurean Experience, complete with a featured cocktail. Then carry on to nearby attractions like the Art Institute of Chicago and the Magnificent Mile’s art galleries.
Where to Eat
Enjoy innovative Mexican food in an art-filled space where the dishes and the vibrant works that line the walls all tell a story. Book on Resy.
This relative newcomer in Chicago’s West Loop is a fast-rising star with global takes on American cuisine – from a signature French onion dip to Japanese sweet potato – in artfully chic digs. Book on Resy.
Visit the Museum of Contemporary Art Chicago to feast your eyes on the masterpieces, then enjoy still more art at this on-site restaurant with an all-day menu, dinner, and even a weekend brunch. Book on Resy.
This stylish West Loop boîte prepares an extended New American tasting menu where the refined culinary arts are on full display via a stunning open kitchen.
A speakeasy-inspired spot with Latinx flair, this funky Little Village bar is attached to a liquor store (enter through a side entrance for that speakeasy feel) and serves cocktails, beer, wine, and Mexican small plates.
What to Do
This traveling global art expo stops in Chicago each fall, inviting art lovers to browse and purchase affordable, original artworks from independent artists and enjoy immersive installations, performances, DJs sets, and more.
This North Side contemporary art museum boasts an extensive collection of dynamic works by some of the globe’s foremost living artists.
Wander through 1,700 acres at this tree-filled botanical garden and research center that also hosts a library and herbarium, along with a variety of temporary art installations throughout the year.
Since 1925, theater buffs have flocked to this minimalist, two-stage venue to take in both classic and original productions.
Music lovers head to this indoor/outdoor multi-use entertainment space along the riverfront for live shows in a renovated space that was once, as the name suggests, a salt factory.
A creative haven stretching west of Fulton Market, Kinzie Industrial Corridor is home to a community of artists and craftspeople, along with their shops and studios with local work for purchase.
Get an inside look at Chicago landmarks on this guided architectural tour with stops including the Rookery, Marquette Building, and Chicago Board of Trade Building.
Fairmont Chicago Millennium Park
Set right by Millennium Park and Lake Michigan, the Fairmont Chicago Millennium Park puts first-time visitors close to some of the city’s biggest attractions, with sweeping skyline views to match. Rooms are spacious and filled with natural light, and there’s plenty to enjoy on-site—from the bold Latin flavors at Toro to a spa with steam rooms and an infinity-edge soaking tub. Step outside and you’re minutes from the Magnificent Mile, Navy Pier, and the Windy City’s renowned greenspaces.
Where to Eat
An upscale steakhouse marked by dark wood and brick accents, Bavette’s channels old-school Chicago and serves a menu of timeless American fare. Book on Resy.
A bustling North Side gathering spot known for its brunch scene, Lula serves an ever-evolving menu of market-driven, seasonal fare. Book on Resy.
A watering hole where Windy City journalists gathered in the 1930s, Billy Goat is now known for its infamous “Cheezborger,” along with an all-day menu of breakfast plates, hot sandwiches, and bar staples.
Lou Malnati’s is known for its classic deep dish, making it a must-visit for Chicago first-time visitors in search of that singularly cheesy bite. No reservations.
A signature cheeseburger is the main attraction at this American restaurant featuring leather booths and a menu of reimagined takes on prime steaks and seafood in an intimate space. No reservations.
There are plenty of spots in Chicago where you can enjoy a good glass of beer. The beauty of The Beer Temple is that it’s a taproom with an adjacent bottle shop — meaning that if you taste something you like, chances are you can buy some to take with you.
What to Do
Chicago has long been synonymous with jazz, and since 1947, the legendary Jazz Showcase has been heralding established stars of the genre as well as up-and-comers, offering live music almost every night of the week.
Even if you’re not a baseball fan, the iconic stadium – home to the Cubs since 1914 – is worth a visit for its history alone.
Chicago’s mirrored Cloud Gate sculpture (aka “the Bean”) is such a hit that New York City had to get its own. Come to snap your Bean selfie here at the original location, then check out more public art and stroll through the park pathways.
Book a scenic tour of the city by water through GetYourGuide.com which offers a variety of cruises, from a 1.5-hour architecture tour to an evening dinner cruise.
As the name suggests, the top of this 94-story tower, delivers 360-degree views of the city, along with the Cloud Bar, a sky-high spot to grab a cocktail with a view.
This famed art museum displays a permanent collection of centuries-spanning works from around the globe and hosts rotating exhibits, along with free daily tours.
Locals and visitors head to this paved 18.5-mile trail along Lake Michigan to birdwatch, bike, jog, walk, or skate – and take in scenic views.
Ways to Earn Points with The Gold Card
The Gold Card offers several Membership Rewards® points-earning opportunities. When you’re ready to travel, you can earn 3X points on flights booked directly with airlines, AmexTravel.com, or the Amex Travel App™. Plus, 5X points on prepaid hotels, and 2X points on prepaid car rentals when you book through AmexTravel.com or the Amex Travel App™. Terms apply.
Get more out of your Chicago getaway with American Express
As an American Express Card Member, make your trip unforgettable with 10% off tours and activities booked at gyg.me/amex from 03/01/26 to 08/31/26. Terms apply.
Get more out of your Chicago getaway with American Express
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