The LoopEditor's pick
Chicago Athletic Association Hotel
4.6(2,847)$$$
Converted 1890s gentlemen's club facing Millennium Park. Library bar, game room, Cindy's rooftop — worth the stay on its own.
from $239 / nightCheck rates
IL · Metro pop. 9.4M
Chicago
The transit city: L trains overhead, Amtrak beneath, architecture everywhere.
A postcard from the city
The L rumbling past the Loop, a deep-dish slice at Pequod's, the sand curving off North Avenue Beach, the wheel turning over Navy Pier, and a frozen winter morning under the river — Chicago shows itself in sections. Give it three days and it starts to hold together.
Rails Midwest · City Guide
Chicago is America's second city and its most transit-obsessed. The 'L' rumbles overhead with a mechanical poetry, Union Station presides over a downtown canyon of Art Deco and modernist towers, and the lakefront sprawls endlessly eastward. It's a city built for movement—from the Illinois Central that brought the Great Migration northward to today's rail-centric urbanism. Come for the architecture tours and deep-dish pizza, but stay because Chicago's walkable neighborhoods and world-class cultural institutions reward extended stays.
ArchitectureCultureFood & DrinkMusicOutdoorsNightlifeArtSports
Orient yourself
Chicago at a glance
The station, airport, and places worth walking to — tap a pin.
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Our picks
Our Recommendations
Where to stay · 4 hand-picked hotels
Hotels
The Loop
The Palmer House Hilton
4.3(8,912)$$
One of the oldest continuously operating hotels in America. The lobby ceiling fresco alone justifies the room rate.
from $179 / nightCheck rates
River North
Virgin Hotels Chicago
4.5(3,104)$$$
Playful boutique with a rooftop pool and a location that puts the River North galleries and dinner scene at your door.
from $209 / nightCheck rates
River NorthBest value
The Freehand Chicago
4.2(1,663)$
Hostel-hotel hybrid with private rooms at dorm prices and the Broken Shaker bar — a top cocktail spot in its own right.
from $99 / nightCheck rates
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What to do · book ahead, skip the line
Experiences
Architecture
Food & Drink
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Getting here
Getting to Chicago
Flying in from abroad, connecting from elsewhere in the US, arriving by Amtrak, or driving in — here’s how each works.
By Air
From the US:O'Hare (ORD) is a United and American hub with non-stop service from virtually every major US airport. Midway (MDW) for Southwest.
From Europe: daily non-stops to ORD from London, Dublin, Frankfurt, Paris, Amsterdam. Customs at Terminal 5 — build buffer before Amtrak connections.
ORD → downtown
CTA Blue Line runs from the ORD stations direct to downtown in about 45 minutes for $5. Union Station (Amtrak) is a short walk from the Clinton stop.
By Train — Amtrak
Union Station is the Amtrak hub of the Midwest. The Lake Shore Limited (Chicago–New York), Empire Builder (Chicago–Seattle), Southwest Chief (Chicago–Los Angeles), and multiple daily trains to St. Louis, Milwaukee, and beyond. Chicago is the nexus of the entire Amtrak network outside the Northeast Corridor.
Connecting on Amtrak: The Hiawatha runs hourly from Milwaukee, the Wolverine and Lake Shore Limited connect from Detroit and the East Coast, and the Borealis / Empire Builder feed in from St. Paul. All deliver you directly to Union Station — no transfer between stations.
Lincoln Service
To St. Louis
5h 20m · 4 daily departures
Wolverine
To Detroit
5h 30m · 3 daily departures
Hiawatha
To Milwaukee
1h 30m · 7 daily departures
Pere Marquette
To Grand Rapids
3h 45m · 1 daily departure each direction
Borealis
To Minneapolis–St. Paul
8h 10m · 1 daily departure
By Car
Union Station's parking garage sits one block south of the station entrance, around $30 a night with multi-day rates. Reserve via SpotHero or ParkWhiz for a meaningful discount on the gate price. Several downtown hotels bundle valet at lower combined rates if you're staying multiple nights.
Good to know
Questions travelers ask
How do I get to Chicago by train?
Fly into Chicago O'Hare (ORD) — a hub for both United and American with non-stop service from virtually every major US airport and most European capitals — or Midway (MDW) for Southwest's domestic network plus secondary international service. Both airports connect to downtown via the CTA 'L' train, and Chicago's Union Station is Amtrak's Midwest hub — trains to every other city on this site depart from there.
How many days do I need in Chicago?
Two to three days suits most travelers — enough to explore architecture, culture, food & drink, and to hit the main neighborhoods without feeling rushed. Add a day if you want to take a day trip out (St. Louis and Detroit are close by rail).
Can I visit Chicago without a car?
Yes — every destination we cover is walkable from its Amtrak station or well-served by local transit. Chicago's downtown is large and transit-connected, and ride-share fills the gaps.