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Plan Your Chicago Holiday: Best of Chicago

What is Travellers’ Choice Best of the Best?
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Chicago’s got the big-city vibes you want, but friendly locals and a walkable layout make it homey and accessible all at the same time. With 77 neighbourhoods to explore, your best bet is starting with the Loop or Gold Coast to hit the highlights, then fan out. Wander among the architecture that made the city famous or eat your way through town. You’ll hear a lot about deep-dish, but the tacos are also next-level, thanks to Chicago’s thriving Mexican community. If you’re there in spring/summer, spend a do-nothing day lounging lakeside or grab a patch of grass at one of its many parks. At night, both the music and comedy scenes have put Chicago on the map. (You can't go wrong, but Lincoln Hall and Second City are always a good time.) There’s lots more to dig into. We’ve got options below.
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Travel Advice

Essential Chicago

A high-low eating tour of Chitown

Chicago is one of the great American restaurant towns, smashing at every level from gravy-drenched sandwiches to molecular theatrics. The city has mastered the high-low food experience like no other and it's what keeps me coming back again and again (I'm a food writer, after all). So if you're like me and love both, here's my list of recs. Bring your appetite.
Adam Erace, Philadelphia, PA
  • Cellar Door Provisions
    High: Cellar Door is clicking again post-pandemic with dinner-only hours and a no-bookings policy. While I miss their exquisite morning pastries (it used to open for breakfast, too), it’s good to be back in this stripped down Logan Square spot. My go to's: the Med-inspired treasures like flat-iron marsala, a white-out of burrata and blanc asparagus, and brown butter-rosemary gelato for dessert. A tip: Get there before they open at five, it gets crowded.
  • Pequods Pizza
    Low: There are plenty of options in town for deep-dish diehards, and this Lincoln Park outpost of Pequod’s is mine. Order a beer or two as you wait (a while) for the ferociously hot pan pizza to land on your table—its ring of caramelized cheese around the rim is gold.
  • Sun Wah BBQ
    High: The Cheng family is Chicago royalty, and Sun Wah is their kingdom. This sprawling institution is iconic and the menu is massive, but the thing to order is not on it: the Beijing duck dinner, a grand multi-course feast (go with a group) starring a roasted duck whose skin is as bronzed and crackled as the top of a crème brûlée. While you can order it once you arrive table, I recommend putting in the request when making a booking.
  • Dove's Luncheonette
    Low: This is the Tex-Mex fantasy diner of my dreams. Crispy hash, brisket tacos on house-made flour tortillas, chicken-fried-chicken, and horchata pie coexist with communal tables, penny-tiled floors, and friendly service. love Dove’s for lunch/brunch, but it’s also a terrific late-night pop-in for al pastor fries and a $5 mezcal shot.
  • Virtue Restaurant & Bar
    High: There are a hundred details that make Chef Erick Williams’s Hyde Park restaurant a pillar of Southern cooking in Chicago. Among them: the smoked turkey perfuming the collards, the turnip chow-chow on the salmon, the Carolina grits with the shrimp and crawfish etouffee. If you can’t get a booking, hang at the bar, which has a stacked wine list, as well as a handful of inventive non-alcoholic cocktails.
  • Johnnie's Beef
    Low: You didn’t think you were getting out of this list without an Italian beef recommendation, did you? Everyone in Chicago has a favourite held close to their heart, but it’s hard to do better than Johnnie’s. Their beef is shaved so thin you can almost see through it, and their giardiniera pops like the Bangsnaps you used to throw at the sidewalk as a kid.It's cash only and a little out of the way in Elmwood Park but so worth it. I like to go on my way to/from O’Hare airport.
  • Mi Tocaya Antojeria
    High: “Nuestro cocina, nuestro amor” (our cooking, our love) is the motto at Mi Tocaya. If you ask me, Diana Dávila is maybe the most talented Mexican chef in a city jam packed with terrific Mexican restaurants. Her colourful, casual dining room in Logan Square is the ideal spot for dishes like braised pork shank in a secret mole sauce and chiles en nogada (made here with Brussels sprouts). Bonus: the drink list is as comfortable around natural wine as it is margaritas.

Chicago Travel Guide

Travelers' pro tips for experiencing Chicago

Mom's Guide To Travel

If you're visiting Chi-Town during the late fall and winter months, dress for brisk and cold weather — hats, scarves, gloves, and a warm outer layer.


Buy a Chicago City Pass that includes several attractions at a very reasonable price.


Chicago is a first-class restaurant city so make reservations as soon as you can. Check out the listings online or in Chicago Magazine.

Mom's Guide To Travel

Chicago has a well-developed transportation system. Getting around is quick and inexpensive. Consider a one-day visitors pass for unlimited bus and train rides.

Diana R

Deep dish pizza isn't meant to be picked up. In fact, sometimes there's so much cheese it just isn't possible! Don't be shy about using a knife and fork — there's no other way.


Chicago is a big city and a lot of history and beauty. Every time I explore the city, I learn and find something new. It's a great city to come and see and spend some time in.


Chicago is a feast for the eyes, the mouth, and the ears.


There are a lot of things to do for the budget-minded traveler. History, architecture, art, food and family activities all can be found for less than you might think in a city like Chicago.

Mom's Guide To Travel

Chicago's location along the waters of Lake Michigan gives it an automatic head start for romance. The Windy City offers couples everything they need to celebrate their affections in a picturesque, diverse, and energetic environment: Historic landmarks, trendy restaurants, iconic skyscrapers, and a vibrant city buzz represent the landscape that is Chicago.

What is the best way to get there?


O'Hare International Airport, 17 miles northwest of downtown Chicago, is a hub for United Airlines. Ten miles southwest of downtown, Midway International Airport is primarily served by low-cost carriers and a few Delta flights. The CTA Blue Line train runs between the Loop and O'Hare every 5-15 minutes, 24 hours a day. The CTA Orange Line train runs between the Loop and Midway from before dawn to after midnight.


Chicago is one of the most convenient U.S. cities to visit by train. Amtrak services from all around the country use Union Station (Canal Street and Jackson Boulevard).


Greyhound, Megabus, and others offer low-cost bus services to Chicago from around the Midwest and beyond.


Drivers usually approach Chicago off the I-90 or I-94. Be prepared for tolls.

Do I need a visa?

If you’re visiting Chicago from overseas, use the State Department’s Visa Wizard to see if you need a visa.

When is the best time to visit?

Spring and fall: The best times to visit Chicago are from April through May and September to October. These seasons bring warm temperatures — a contrast to the sweltering heat of summer and bitter cold of winter. Spring temperatures typically range from the mid-50s°F (12.7°C) in April to around 70°F (21°C) in May. Fall temperatures average around 70°F (21°C) in September, drop into the low 60s°F (15.5°C) in October.

Get around

on foot

Downtown Chicago is very walkable. In the winter months, the Chicago Pedway System leads walkers through a system of passages that connect buildings and let them avoid the cold.

l train

The L (a system of elevated and subway trains) is fast, frequent and will get you to most top attractions. Purchase a Ventra Ticket at station vending machines or a Ventra Card, which you can recharge and save money with.


Metra commuter trains run on 12 routes serving the suburbs from four terminals ringing the Loop. Buy tickets from agents and machines at major stations.


City buses are useful for getting to certain locations including Hyde Park and Lincoln Park’s. You can use a Ventra Card or pay the driver with exact change. Buses are particularly useful for reaching the Museum Campus, Hyde Park, and Lincoln Park Zoo.


Taxis are plentiful, inexpensive, and can be hailed on the street almost anywhere.


Divvy is Chicago’s bike-sharing program. Its blue bikes can be found at 580 stations around Chicago and the neighboring suburbs. A day pass allows unlimited rides in a 24-hour period, up to three hours each, or you can buy a single-ride pass that is good for 30 minutes.


Uber and Lyft are available in Chicago on your smartphone.


Driving in downtown Chicago should be avoided if possible: Traffic is almost always heavy, parking is expensive, and drivers tend to be aggressive.

On the ground

What is the timezone?

Central Daylight Time

What are the voltage/plug types?

The standard voltage in the United States is 120 V and the standard frequency is 60 Hz. The plug has two flat parallel pins.

What is the currency?

The U.S. dollar

Are ATMs readily accessible?


Are credit cards widely accepted?


Is it easy to find a bank?


How much do I tip?


$1 a drink or $2 for a more labor-intensive cocktail




$1 to 3 per bag


$2-$3 per night



Shuttle driver

$1-$2 per person

Tour guide


Are there local customs I should know?


The federal legal age for buying and drinking alcohol is 21 years old.


Stand to the right on the escalators; walk on the left.

Hot dogs

Chicago takes its hot dogs seriously and it’s a local rule that you don’t put ketchup on them.


Walk to the right of the sidewalk and step off to the side of the sidewalk if you want to stop to check your phone, look up directions, or want to take in a view.

Public transport

Allow others to disembark before boarding, don’t take up more than one seat and stand to offer seating to pregnant women or someone with a disability.


Spitting is considered rude in any public setting.

Find more information about local customs and etiquette in the United States generally here.