Photo by A. Duarte

Chicago Itineraries

Chicago for Kids and Families

Chicago in 48 Hours

Chicago’s Green Dining Scene

Chicago’s Underbelly: A Literary Survival Guide

The Windy City blows you away with sky-high architecture, fab food and world-class museums

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Rising up smack in the middle of the country, big and brawny and quick on its toes, Chicago is often cited as the most American of cities. This is the place that invented the skyscraper, and its lofty buildings roll out views that’ll buckle your knees. Star collections of art, dinosaurs and science baubles stuff its enormous museums. Awesome food hits its tables at reasonable prices, which is why chowhounds troop here during all seasons.

Need more reasons to visit? Sand-and-surf beaches edge the city along vast Lake Michigan. Groovy entertainment rocks the town, with booze-fueled improv comedy, poetry slams and blow-the-roof-off bands on stages nightly. And there’s no better place to see a baseball, basketball, hockey or football game, as Chicago fans are legendarily diehard, steeped in tradition and curses (and beer).

A patchwork of neighborhoods comprises the city. Clattering El trains roar downtown, dropping you into a sky-high forest of steel and stone. The Loop is the hustle-bustle heart of it all, home to the top-draw Art Institute, Millennium Park, Willis Tower and Chicago Architecture Foundation tours. Next door the South Loop holds the Field Museum and Shedd Aquarium, while the West Loop is where Chicago’s hottest chefs cook.

Nearby, Near North and Lincoln Park offer attractions such as Navy Pier and Lincoln Park Zoo. Farther on, Lake View and Wrigleyville are great ‘hoods for energetic eating and drinking spots, and retro Wrigley Field is a must for baseball fans.

Other neighborhoods worth a visit include Wicker Park and Bucktown (for hip restaurants and record shops), Logan Square and Humboldt Park (for low-key Michelin-starred eateries and cool cocktail bars), Chinatown and Pilsen (for ethnic eats and vintage shops) and Hyde Park and South Side (for museums and comfort food).

Explore a Chicago Itinerary:

To hit the highlights, see Chicago in 48 Hours.
To experience the city with children, see Chicago for Kids and Families.
Chicago’s Green Dining Scene … A healthy guide to good eats
Chicago’s Underbelly: A Literary Survival Guide … An alternative introduction to experiencing Chicago

No matter what your age or time frame for visiting, know this: Chicago is the one town that won’t let you down.

When To Go

You can visit Chicago any time of year, but know that weather and crowds can impact your stay. Winter (December through March) is cold and windy, but prices are rock bottom. Summer (June through August) brings lovely weather, beaches, baseball and festivals galore, but also throngs of people and peak prices. Spring and fall are good shoulder season times to visit.

The exception to this is if there’s a big convention in town, which can wildly increase hotel rates. Beware of the following:
* International Home and Housewares Show: 3 nights in mid-March
* National Restaurant Association: 3 nights in mid-May
* American Society of Clinical Oncologists (ASCO): 5 nights in late May/early June
* Radiological Society of North America: 5 nights in late November/early December

Events such as Blues Fest (mid-June), Lollapalooza (early August) and the Chicago Marathon (mid-October) also bring crowds and affect prices.

How Much Time To Spend

48 hours will give you a good bite of Chicago.You can hit several highlights in that time. But add another day or two to take full advantage of the city’s neighborhoods, food and nightlife.

High and Low Season

Summer (Jun-Aug) is peak tourism season thanks to warm weather and Chicago’s rollicking festival lineup. Hot and humid days crop up, but it’s usually quite comfy – perfect for hitting the local beaches. You might have to wait in line at some of the main attractions.

Winter (Dec-Feb) is low season. It’s cold and often snowy, but still manageable. Do like the locals do: bundle up and head to the public ice rinks. Hotels, restaurants, theaters and other entertainment venues offer terrific bargains, and crowds are nil.

Spring (Mar-May) and Autumn (Sep-Nov) are the shoulder seasons. They’re a mix weather-wise: you might wake up to a frosty day, or a beautiful warm sunny day. If it’s the latter, everyone races out to the parks and lakefront path.

Weather and Climate

For today’s weather and a five-day forecast for Chicago, click here.

Seasonal specifics:

* Winter: 37 inches (949 mm) average snowfall, 30 – 38°F (-1°C – 3°C) daily high temperature.

* Spring: 50’s °F (10-15°C) on average in April, around 70°F (21°C) in May. Both months see a fair amount of rain.

* Summer: 78°F to  92°F (26°C – 33°C) during the day (though it’s typically cooler by the lake). This is the rainiest season, with 3.7 – 4.3 inches (94 to 109mm) of the wet stuff falling per month.

* Fall: Daytime temperatures around 70°F (21°C) give way to the mid-40’s (7°C) as winter approaches.

Events and Holidays

Top Events

Blues Fest (mid-June)
Taste of Chicago (mid-July)
Pitchfork Music Festival (mid-July)
Lollapalooza (early August)
Jazz Fest (early Sep)
Chicago Marathon (mid-October)

National and State Holidays

January 1: New Year’s Day
January (third Monday): Martin Luther King Jr. Day
February 12: Lincoln’s Birthday
February (third Monday): Presidents Day
March (first Monday): Casimir Pulaski Day
May (last Monday): Memorial Day
July 4: Independence Day
September (first Monday): Labor Day
October (second Monday): Columbus Day
November 11: Veterans Day
November (fourth Thursday): Thanksgiving Day
December 25: Christmas

Time Zone

Chicago is located in the Central time zone. To check the local time in Chicago, click here.

Daylight Savings Time (DST) happens in spring on the second Sunday in March, when clocks are advanced one hour. In the fall on the first Sunday in November, clocks shift back one hour to standard time. The entire U.S. (except Hawaii and most of Arizona) participates in this ritual of ‘springing forward’ and ‘falling back.’

What To Pack and Wear

Chicago is an informal town. The height of dressing up for most men is a pair of khakis and a button-down shirt. Women’s fashion is similarly low-key, valuing comfort over high couture. It’s perfectly fine to wear jeans and casual cloths to dinner or the theater at night.

What it Costs

Chicago provides pretty good bang for the buck. Lodging will be your biggest expense. Expect to pay $150-$250 per night for a hotel room in non-peak season (September through May). That goes up to $200 to $300 in peak season (June through August). But prices can ratchet up any time of year if a big convention comes to town.

Eating out in Chicago is cheap compared to other big cities. You can get plenty of great meals for under $15. Expect to pay $20 to $30 for dinner in the many casual-trendy-foodie-type restaurants the city is known for.

Admission to top-tier museums hovers around $25, but the city offers loads of free museums and activities you can take advantage of. Seeing live music at a club typically costs $10 to $20, though again, many venues are free. Cubs tickets cost around $40, as does an architecture tour by boat.

Abstract Pricing at a Glance

Prices often fluctuate dynamically depending on capacity, seasonality and deals. We don’t want to lead you astray by quoting exact prices that quickly become wrong. To give you a rough idea for budgetary planning purposes, though, we have indicated general price ranges for all points of interest.

Price ranges are quoted in $US.

See & Do
N/A => Not applicable
$ => Tickets less than $10 per person
$$ => Tickets $11-25 per person
$$$ => Tickets $26 per person

$ => Rooms less than $100 for a double
$$ => Rooms $200 for a double
$$$ => Rooms $300 for a double

$ => $1-15 per person for a meal (without alcohol, tax, tip)
$ => $16-40 per person for a meal (without alcohol, tax, tip)
$$$ => $41 per person for a meal (without alcohol, tax, tip)

N/A => Not applicable

$ => Tickets less than $10 per person
$$ => Tickets $11-25 per person
$$ => Tickets $26 per person

Airfare and Car Rental Prices


Airfares are a fickle thing. When you need it to be low, it’s high. And when prices dip, what happens? You can’t get off work to travel. Sigh.

But you can get notifications from companies like Kayak, which will email you when airfares drop. Type your destination and the dates you are watching and boom, when there’s a deal, you’ll hear about it immediately via your inbox.

Sites like Momondo also display prices for multiple airlines, so you can compare rates without visiting individual airline sites.

That said, there is an advantage to visiting an individual airline’s site. Why? Because some of their really great deals don’t show up on the aggregator airfare sites. Most airlines share limited-time, super-specials via their Facebook pages or email blasts. So it pays to be their ‘friend’ or subscribe to their e-mailings.

Car Rentals

For Chicago’s main sightseeing neighborhoods you don’t need a car. In fact, a car is an expensive hassle. Parking garages cost around $40 per day. Street parking can be scarce, and when you do find it, metered parking costs $2 per hour (in outlying areas) to $6.50 per hour (downtown). Rush hour traffic is typically jammed. Public transportation is a much better option.

But if you must rent a car, know that rates are all over the map. Companies like Expedia and Hotwire offer comparison price shopping.

Did You Know: Budget Car Rental offers drivers residing at the same address (i.e. unmarried partners or BFFs) complimentary extra driver coverage. Other car rental companies charge upwards of $10/day. By the way, when renting in California, there are no additional driver fees by law.


Ride-sharing companies Uber and Lyft are ubiquitous in Chicago. Download their apps to line up rides all over town.


Hopefully, your trip to (or within) the U.S. goes without a glitch. But what if an unexpected situation arises? Will you lose the money you invested in the trip? Will you need quick cash to cover sudden costs?

Travel insurance policies are meant to cover these unexpected costs and assist you when problems arise. The fee is typically based on the cost of the trip and the age of the traveler.

Most travel insurance providers offer comprehensive coverage that usually includes protection for the following common events:

Trip Cancellation: About 40 percent of all claims fall in this category.

Medical: Health services in the U.S. are expensive for the uninsured. This is a major reason to consider purchasing insurance. Whether you break a leg or need a blood transfusion, you will likely incur costs far higher than you might pay in other nations. And what if you have an accident that requires transport to a major medical center? Air ambulances alone could set you back $15,000 to $30,000.

Trip Interruption: For example, if you become ill during your trip or if someone at home gets sick, and you have to get off the cruise ship or abandon a tour. The insurer will often pay up to 150% of the cost of your trip to get you home.

Travel Delay: Insurance usually covers incidentals like meals and overnight lodging while you wait to travel home.

Baggage: Insurance will typically cover lost and mishandled baggage.

Some insurance companies allow you to purchase a policy that allows you to cancel for any reason. This may cost more (often 10% or more), but it is worthwhile for certain travelers.

Do I need travel insurance?

If your trip costs $4,000 to $6,000 (or more), it’s probably a good idea. Your age and health are important factors. So is your destination. If you’re traveling to a hurricane-prone area during hurricane season, for example, you’ll probably want some coverage “just in case” … no matter what.

Your English language skills are also an important factor. Insurance policies often include concierge services with 24-hour hotlines that can connect you quickly with someone who speaks your language.

How do I choose an insurance provider?

Do your homework; check around.

The largest insurers in the U.S. include Travel Guard, Allianz and CSA Travel Protection. Smaller reputable companies include Berkley, Berkshire Hathaway Travel Protection, Travel Insured International and Travelex. You may also find deals through aggregator sites like Squaremouth and InsureMyTrip.

Many airlines and travel companies also offer travel insurance when you book your flight (often contracted with the above major players).

If you have pre-existing health conditions: Many policies have exclusion policies if you have a pre-existing medical condition. But companies also offer waivers that overwrite the exclusion if you purchase the policy within a certain time frame of paying for your trip (e.g., within 24 hours of buying your cruise package). Again, it’s best to check the fine print.

Credit card insurance: If you buy your airfare or trip with a credit card, you may be partially covered by the credit card’s issuing bank. Check directly with the company to find out exactly what’s covered, as many have “stripped down” coverage and restrictions.

The travel insurance business is expanding and evolving rapidly. As “shared space” lodging options like VRBO, Airbnb and Homeaway become more popular in the travel and leisure market, so does the need for insurance for both property owners and travelers.

For more information, visit the US Travel Insurance Association.

Exchange Rates and Currency


Chicago uses the U.S. dollar. U.S. dollars come in $1, $5, $10, $20, $50 and $100 bills. They are all the same size and color, so non-Americans have an understandably tricky time telling them apart. The $2 bill is in circulation but rarely seen.

Coins in wide circulation include the penny (one cent), nickel (five cents), dime (ten cents) and quarter (25 cents). The 50-cent and one-dollar coins are seen occasionally.

Smaller businesses may not accept $50 or $100 bills, so have twenties or smaller bills in hand. ATMs usually dispense $20 bills.

For current exchange rates, check xe.com.

Tipping and Costs That Add Up

Tipping is a cost you must build into the budget for any U.S. travel experience, whether urban or rural. Tipping is most relevant to dining out and hotel stays, but other costs should also be taken in to consideration. General guidelines include:


For excellent service, plan to tip 20% on the total bill, before taxes. For less-than-stellar service, 10-15% is customary, as an imperfect experience is often not solely the responsibility of the server. In many states, servers work for below minimum wage and live mostly on tips, so consider the ramifications of your tipping decisions.

To complicate matters, many restaurants in the major metropolitan areas — including a few in Chicago — are moving to a no-tipping model in which service is included. The verdict isn’t yet in on whether this new model will stick, so be sure you understand the tipping policy at each restaurant you visit.

Oh, and one more complication: Sometimes a tip is automatically included, usually for groups of six or more people. But at least it will be itemized in plain sight on the bill, if you look closely for it.


Most bell staff receive $1 to $2 per bag they assist with; if someone carts all of your bags up to your room, expect to tip $5 to $10.

Tips for housekeeping are also good form. The rule of thumb is $2 to $3 per day and about $5 per day in higher-end properties.

At properties with concierge services, consider tipping concierge staff who assist you in planning activities, making reservations or acquiring tickets around $10 to $20 per day. Concierge staff do not normally expect a tip for simply orienting you with driving directions or public transportation info. Car valet staff expect $2 when returning your car. Spa employees (massage therapists, aestheticians, etc.) usually see 20% tips on their services, whether performed at the spa or in your room.


Sales tax on retail goods and services ranges from 10.25% to 11.25%.

Lodging tax in Chicago is 17.4%. This tax applies whether you are staying at a private vacation rental, a bed-and-breakfast, or a full-fledged hotel. Taxes are not usually stated up front in the advertised room rate.


Chicago is a transport hub. It’s easy to get here by plane, train or automobile.

There are two airports:

O’Hare International Airport (ORD) is larger, and among the world’s busiest. It’s the headquarters for United Airlines and a hub for American. Most international flights use it. It’s 17 miles northwest of downtown.

Midway Airport (MDW) is smaller and used mostly by domestic carriers, such as Southwest. It’s 11 miles southwest of downtown.

Trains chug into Union Station downtown. Megabus also arrives at Union Station. The Greyhound station is a bit southwest of downtown.

Once you’re in town, public transportation – mainly the El trains – will get you where you need to go. The city’s bikeshare program is another option. Taxis, Uber and Lyft also do the job.

Getting There

From O’Hare International Airport

* The cheapest and often quickest way into the city is the CTA Blue Line train ($5), which runs 24/7. Trains depart every 10 minutes or so; they reach downtown in 40 minutes. Can be desolate in the wee hours.

* Airport Express shared shuttle vans cost $32. They operate between 4am and 11:30pm, departing every 15 minutes. They drop off at your hotel. They reach downtown in 60 minutes or so.

* Taxis cost around $50. Taxi queues can be lengthy, and the ride can take as long as the train, depending on traffic.

From Chicago Midway Airport

* The cheapest and often quickest way into the city is the CTA Orange Line train ($3). Trains depart every 10 minutes or so; they reach downtown in 30 minutes.

* Airport Express shuttle vans cost $27. They operate between 4am and 10:30pm, and take 50 minutes to reach downtown hotels.

* Taxis cost $35 to $40 and take 20 minutes or more (depending on traffic).

From Union Station

It’s at downtown’s western edge, and is a bit of a hike from where the majority of hotels are located. Several taxis queue along Canal St; a ride to most hotels costs around $10.

Getting Around

By Elevated/Subway Train

* Chicago’s El (it stands for ‘elevated,’ though many trains also run underground) is the main way to get around.

* Two of the eight color-coded lines – the Red Line, and the Blue Line to O’Hare airport – operate 24 hours a day. The other lines run from 4am to 1am daily.

* The standard fare is $3 (except from O’Hare, where it costs $5) and includes two transfers.

* Enter the turnstile using a Ventra Ticket, which is sold from vending machines at train stations.

* You can also buy a Ventra Card, aka a rechargeable fare card, at stations. It has a one-time $5 fee that gets refunded once you register the card. It knocks 75 cents to $1 off the cost of each ride.

* The Chicago Transit Authority has El and bus schedules on its website, plus a useful trip planning feature.

By Bus

* City buses operate from early morning until late evening.

* The fare is $2 (cash accepted, but no change is given).

* Ventra Cards (see Train, above) can also be used.

By Taxi or Rideshare

* Cabs are plentiful downtown and in surrounding neighborhoods.

* Fares are meter-based. The meter starts at $3.25, then it’s $1.80 per mile and $1 per extra passenger.

* Yellow Cab (312-829-4222) is reliable.

* Uber and Lyft are also much used in town.

By Bicycle

* Chicago has a bikeshare program called Divvy www.divvybikes.com, with  more than 3000 sky-blue bikes at stations around town.

* Kiosks issue 24-hour passes ($10) on the spot. Insert a credit card, get your ride code, then unlock a bike.

* The first 30 minutes are free; after that, rates rise fast if you don’t dock the bike.

* Bike rentals for longer rides (that include helmets and locks) start at $18 per two hours. Try Bike Chicago or Bobby’s Bike Hike.

By Car

* Parking garages cost around $40 per day.

* Street parking can be scarce, and when you do find it, metered parking costs $2 per hour (in outlying areas) to $6.50 per hour (downtown).

* Rush hour traffic is typically jammed.

* Read signs carefully, as some streets are for residents only (visitors must have parking passes).

Discounts and Passes

If you’re going to use the El more than a few times, it’s worth it to buy a rechargeable Ventra Card, available at any El station. You can add value as needed. Without a Ventra Card, each ride you take is subject to a surcharge (around $1) for using a disposable ticket.

Unlimited ride passes (one-/three-day pass $10/20) are also available; get them at rail stations.


In the late 17th century, the Potawatomi gave the name Checagou – meaning wild onions – to the once-swampy environs. The new city’s pivotal moment happened on October 8, 1871, when (so the story goes) Mrs O’Leary’s cow kicked over the lantern that started the Great Chicago Fire. It torched the entire inner city and left 90,000 people homeless.

Instead of wallowing in despair, the city used the tragedy as an opportunity. City planners rebuilt with steel and created space for bold new structures, such as the world’s first skyscraper, which popped up in 1885. In the years that followed, Chicago continued to give the world inventions such as the Ferris wheel, the brownie, the zipper, birth control pills, the electric blues and deep-dish pizza.

A spirit of innovation lingers. Today you’ll see it in groundbreaking theater productions, chefs’ bubbling kitchens and the awesome architecture that continues to rise from city streets.

To get in the Chicago mood, check out the following lists of:
* Books
* Movies
* Tunes
* Websites


Here are translations for a bit of local slang:

LSD: Lake Shore Drive; also called “The Drive.”

The Ike: The Eisenhower Expressway (aka I-290).

A Polish: Short for a Polish sausage sandwich (or sammich, as the case may be).

Wet: How to order extra juice on your Italian beef sandwich.

Ventra: The bus and train fare payment system.

Dibs: Local code of saving a street parking spot with a household object (say, milk crates or old chairs) after you’ve shoveled said spot free of snow. No one else is allowed to remove the objects and park there.

Recommended Reading


The Coast of Chicago (1986), by Stuart Dybek
The Man with the Golden Arm (1949), by Nelson Algren
The Adventures of Augie March (1953), by Saul Bellow
The Jungle (1906), by Upton Sinclair
Native Son (1940), by Richard Wright
A Street in Bronzeville (1945), by Gwendolyn Brooks
The House on Mango Street (1984), by Sandra Cisneros


The Third Coast (2013), Thomas L Dyja
The Devil in the White City (2003), by Erik Larson
Chicago: City on the Make (1964), by Nelson Algren
One More Time (1999), by Mike Royko
Division Street: America (1967), by Studs Terkel


Movies about Chicago, in order of awesomeness:

Ferris Bueller’s Day Off (1986)
The Untouchables (1987)
The Blues Brothers (1980)
Hoop Dreams (1994)
Cadillac Records (2008)
Public Enemies (2009)
High Fidelity (2000)
About Last Night (1986)

Soundtrack for a Road Trip

Wang Dang Doodle, by Koko Taylor
Fever, by Buddy Guy
Via Chicago, by Wilco
Sweet Home Chicago, by Robert Johnson (The Blues Brothers)
My Kinda Town, by Frank Sinatra
Champagne & Reefer, by Muddy Waters
Rocket Ride by Felix, Da Housecat

Websites and Maps

Choose Chicago: The city’s official tourism website.

Chicagoist: Covers local food, arts and events with a dose of sass.

Chicago Reader: Free alternative newspaper with comprehensive arts and entertainment listings.

Chicago Tribune: The city’s more conservative daily newspaper.

Chicago Sun-Times: The city’s more tabloid-y daily newspaper.


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