My answers to some questions frequently asked by FlyerTalkers about Chicago. Since I usually fly United, answers focus on O’Hare’s Terminal 1; since I don’t drive, I’m assuming you won’t, either. Incidentally, my first visit to Chicago — and, in fact, only visit before I decided to move here — was a night spent at ORD due to a weather cancellation on a LAX-ORD-RDU trip on AA many years ago. Updated on a regular basis in response to new questions and/or inbound search inquiries.

What can I do at the airport?
First, check out this helpful “best of the airports” guide from Time Out Chicago (large PDF). Also check out the official airport guides. Also, see the answer for “landside” below, if your bags are checked through and you want to leave the airport bubble. (Since those guides were printed, a pleasant Mediterranean takeaway has opened near B5.)

How do I get between ORD terminals? There are airside walkways between T1, T2, and T3, but the signage isn’t always that great. The walkways are close to the landside; as you approach the security lanes (don’t go through!), look left/right for the inter-terminal walkways. You really should only use the train to get to/from T5, since the hassle of going back through security will eat up any time savings. (For more about international connections, see this FT post.)

In T1, look across from gate B5/B6 for the walkway to T2. In T2, from gate E1, look to the left towards the Cinnabon for the walkway to T1; from the Hudson (?) News next to F1, look right toward the kids’ play area for the walkway to T3. In T3, follow the signs to Concourse G; the passage to T2 is on the right. If you’re connecting from concourse C to T2, use the United bus shuttle between C9 and E3. There are small signs directing you down the stairs.

How do I use ground transportation to get between airports?
There are shuttles between ORD and MDW, but I’ll focus on transit since it’s what I know best.

• To/from ORD, take the CTA Blue Line, which runs 24/7. This interchanges with the Orange Line at Clark/Lake downtown, and with Union Station (Amtrak) at Clinton, also downtown.
• To/from MDW, take the CTA Orange Line, which runs 4 AM – 1 AM. The nearest station to Union Station (Amtrak) is Quincy, which is several blocks east of Union Station. The outlying airports are probably better done by rental car, although I’ve transit-ed them as trials of my willpower.
• MKE is on Amtrak’s Hiawatha line between Chicago and Milwaukee; there are seven trains daily to/from Chicago Union Station. (Buses are also available; see this page for details.)
• SBN (South Bend) is at the end of the South Shore commuter line, which is a very long ride from downtown Chicago’s Millennium Park station. (Millennium station is an underground commuter rail station with an entrance at Michigan & Randolph, a few blocks east of the Orange Line’s Randolph and Blue Line’s Washington stations.)
• I am one of few Chicagoans to have ever attempted a bus trip to RFD: a Van Galder Lines bus from ORD’s efficient Bus Center to suburban Rockford, then RMTD’s East State bus into downtown and South Main to the airport. It took forever, but was worth it for that infamous RFD airport promo. (Van Galder runs very frequent and dependable service to Rockford.)
• STL is a good eight or so hours across Illinois: go to Chicago Union Station, take either Amtrak or Megabus (must be booked online) to St. Louis Union Station, and Metrolink from there to STL’s terminal. You can see the Metrolink station from Amtrak’s station; from Megabus’ dropoff, it’s off to the right.
• I have not yet had reason to fly out of MSN, but it is theoretically possible to get there by Van Galder + Madison Metro; nor have I yet gone to IND.

Which ORD security lines are fastest?
The ones at the ends of the ticketing halls. In T1 and T3, walk all the way to the left; in T2, walk all the way to the right. (UA travelers even report that this line at T1 is faster than the Premier line; it also drops you off right in front of the low-numbered B gates, which UA usually uses for Business1 flights.)

What can I do landside, perhaps while awaiting an arriving passenger? The O’Hare Hilton has a bar, some shops, and a gym with day passes available. Otherwise, there are now a few Starbucks kiosks by the baggage claims, and T5’s food court (unlike SFO, it’s nothing special — except that it houses the only Gold Coast Dogs in the airport) is also before security. Is there an airside post office at ORD? Not anymore, although there’s still a stamp vending machine where it was (near the entrance and playground at T2). FedEx has drop boxes in the B-concourse RCC and the H-K Admiral’s Club. There’s a blue postbox by gate B14 in T1.

Is there free wi-fi?
The airport wi-fi has free access to a limited menu of sites. American’s Admirals Club has free wi-fi, which you might be able to pick up outside the doors; you might also try airport McDonald’s locations.

Where can I find local draft beer?
Two good options: Berghoff, Wisconsin-brewed but still a Chicago tradition, has a great space out by C26; local brewpub Goose Island has a kiosk in T2 (on the walk towards T1) and a bar near C10.

Where should I stay?
Downtown. If you can’t afford to stay downtown, then an airport hotel (with shuttle to the airport and thus CTA) is a distant second bet. Almost none of the suburban hotels have adequate transit service; the few in Evanston are the only exception. As a rule, the large South Loop hotels tend to be cheaper than those along N. Michigan, and offer better transit access (assuming you’re not going to spend your time in the Michigan Avenue tourist ghetto). If you are staying along Michigan Avenue and want to head to the North Side, consider using the express bus routes headed north along Michigan instead of the Red Line. If all you want is a basic hotel, and if you don’t have existing hotel affinities or have a particular conference/location in mind, there’s no reason not to use Priceline or Hotwire (aka “opaque channels”) to get a hotel room. The rates really are cheaper. There are no fleabag hotels in their systems. (Hint: BetterBidding has a key by which you can identify Hotwire’s hotels.) If you have to stay near the airport, try the Airport Hotel Guide. Since they’re all the same and all have airport shuttles, go ahead and use an opaque channel — or, if you’ve been stranded tonight, ask an airline rep for a “pink voucher,” which might get you an even cheaper rate.

Where should I park?
Near O’Hare, park at the Cumberland Blue Line station and take the train to either O’Hare or the city; it’s $12/day. If you have to bring your car downtown, the garages under Grant/Millennium parks are probably the best deal going. You will not find cheap parking near Michigan Avenue; sorry, that’s life.

I’ve got several hours here and want to explore. Where should I go?
Good for you! The food’s much better outside the airport, I can assure you. From ORD, take the Blue Line to Logan Square, Damen, or Division. You’ll save at least half an hour off the train trip all the way downtown, and see some cool neighborhoods (with better, cheaper food/drink than downtown). MDW is just half an hour from the Loop; Library and Madison/Wabash are among the more interesting stopping off points.

That’s all well and good, but I’m here at weird times.
You’ve got a few overnight and early-morning options just off the Blue Line (which runs 24/7). There’s a 24-hour supermarket a block from the Division station: Jewel/Osco, behind Bank of America at the NW corner of the intersection. For basic diner food, hop off at Harlem for Mr. K’s or Belmont for K&S. At Western, you’ve got your choice of Mexican joints (and you’d be surprised at the quality; Chicago has America’s second-largest Mexican population): Arturo’s and Lazo’s are side by side, almost next to the station. In the same vein at Logan Square, there’s Mi Familia and Taqueria Puebla. And for slightly better food, the Blue Angel is a few blocks from the Jefferson Park station.