Orbitz is pleased to offer airline tickets on American Airlines, which operates a daily non-stop flight from Anchorage (ANC) to Chicago (ORD) regularly scheduled to depart at 9:43pm and arrive at 6:35am. Usually a Boeing 737 is flown for this route. The average travel time from Anchorage, AK to Chicago, IL is 5 hours and 52 minutes.

Quick Flight Searches
Weekend Trips - Search
Upcoming weekend flight specials and airline deals on flights to Chicago (ORD) from Anchorage (ANC) Weekend travel in February from ANC to ORD Weekend travel in March from ANC to ORD Weekend travel in April from ANC to ORD Vice versa? Search for last minute deals on airline tickets from Chicago (ORD) to Anchorage (ANC) Weekend travel in February from ORD to ANC Weekend travel in March from ORD to ANC Weekend travel in April from ORD to ANC
Great Travel Deals Anytime - Search
Save money when you book a Chicago Vacation Package here Need a discount hotel room in Chicago? Click here Find airport hotel rooms near Chicago -- click here Reserve your rental car in Chicago -- click here Let DealDetector watch for deals from Anchorage to Chicago

Regularly Scheduled Flights to Chicago (ORD) from Anchorage (ANC)
				Daily Non-Stops		Select Non-Stop		Earliest Flight		Last Flight
	American Airlines			1		-		9:43pm		9:43pm
	Alaska Airlines			1		-		9:43pm		9:43pm

During your Chicago vacation, don't miss these great establishments and attractions:

Navy Pier
Built during World War I, this 3,000-foot-long pier was used by the Navy during World War II as a training center for pilots. But any military aura is long gone, now that the place has been transformed into a bustling tourist mecca. A combination of carnival, food court, and boat dock, the pier makes a fun place to stroll (if you don't mind crowds), but you'll have to walk all the way to the end to get the best views back to the city.Midway down the pier are the Crystal Gardens, with 70 full-size palm trees, dancing fountains, and other flora in a glass-enclosed atrium; a white-canopied open-air Skyline Stage that hosts concerts, dance performances, and film screenings; a carousel; and a 15-story Ferris wheel that's a replica of the original that debuted at Chicago's 1893 World's Fair. The 50 acres of pier and lakefront property also are home to the Chicago Children's Museum, a 3D IMAX theater (tel. 312/595-5629), a small ice-skating rink, and the Chicago Shakespeare Theatre. The shops tend to be bland and touristy. Dining options include a food court, an outpost of Lincoln Park's popular Charlie's Ale House, and the white-tablecloth seafood restaurant Riva. You'll also find a beer garden with live music; Joe's Be-Bop Cafe & Jazz Emporium, a Southern-style barbecue restaurant with live music that is run by Joe and Wayne Segal of Jazz Showcase fame; and Bubba Gump Shrimp Co. & Market, a casual family seafood joint. Summer is one long party at the pier, with fireworks on Wednesday and Saturday evenings.The Smith Museum of Stained Glass Windows may sound incredibly dull, but decorative art aficionados shouldn't miss this remarkable installation of more than 150 stained-glass windows set in illuminated display cases. Occupying an 800-foot-long expanse on the ground floor of Navy Pier, the free museum features works by Frank Lloyd Wright, Louis Sullivan, John LaFarge, and Louis Comfort Tiffany.Navy Pier hosts a variety of conventions and trade shows, including an international art exposition in May, pro-tennis exhibitions, and a flower and garden show. There's something for everyone, but the commercialism of the place might be too much for some people. If that's the case for you, take the half-mile stroll to the end of the pier, east of the ballroom, where you can find a little respite and enjoy the wind, the waves, and the city view, which is the real delight of a place like this. Or unwind in Olive Park, a small sylvan haven with a sliver of beach that lies just to the north of Navy Pier.You'll find, moored along the south dock, more than half a dozen different sailing vessels, including a couple of dinner cruise ships, the pristine white-masted tall ship Windy, and the 70-foot speedboats Seadog I, II, and III. In the summer months, water taxis speed between Navy Pier and other Chicago sights.Allow 1 hour.

Chicago Trolley Company
Chicago Trolley Company offers guided tours on a fleet of rubber-wheeled "San Francisco-style" trolleys that stop at a number of popular spots around the city, including Navy Pier, the Grant Park museums, the historic Water Tower, and the Sears Tower. You can stay on for the full 1 1/2-hour ride or get on and off at each stop. The trolleys operate year-round, but winter visitors won't need to wear a snowsuit; the vehicles are enclosed and heated during the chilliest months. The same company also operates the Chicago Double Decker Company, which has a fleet of London-style, red, two-story buses. The buses follow the same route as the trolleys; if you buy an all-day pass, you can hop from bus to trolley at any point.

Ravinia Festival
Want to know where the natives get away from it all? Come summertime, you'll find us chilling on the lawn at Ravinia, the summer home of the highly regarded Chicago Symphony Orchestra in suburban Highland Park. The season runs from mid-June to Labor Day and includes far more than classical concerts: You can also catch pop acts, dance performances, operatic arias, and blues concerts. Tickets are sold to both the covered pavilion, where you get a reserved seat and a view of the stage, and the lawn, which is the real joy of Ravinia: sitting under the stars and a canopy of leafy branches while listening to music and indulging in an elaborate picnic (it's a local tradition to try to outdo everyone else by bringing candelabras and fine china). I've been here for everything from Beethoven symphonies to folky singer-songwriters, and the setting has been magical every time. The lawn to the left of the stage is a popular place for families to spread out, but I'm partial to the tree-filled area on the right (the lights projected into the branches create a dramatic effect after the sun sets).Don't let the distance from downtown discourage you from visiting, because Ravinia is served by an extremely convenient public-transportation system. Any evening a concert is scheduled, a special Ravinia Metra commuter train leaves at 5:50pm from the North Western train station at Madison and Canal streets (just west of the Loop). The train stops directly at the festival at 6:30pm, plenty of time to enjoy a picnic before an 8 o'clock showtime. After the concert, trains wait right outside the gates to take commuters back to the city. The round-trip train fare is $5, a real bargain considering that traffic around the park can be brutal.Dining options available at the park range from the fine-dining restaurant Mirabelle (tel. 847/432-7550 for reservations) to prepacked picnic spreads from the Gatehouse, featuring gourmet items to go. For $10, you can rent a pair of lawn chairs and a table from booths set up near the park entrance. In case you're wondering about the weather conditions at concert time, dial Ravinia's Weather Line (tel. 847/433-5010).

Make your reservations for discount hotel rooms in the Chicago area, including:

Holiday Inn-Chicago City Centre
Enter the soaring modern atrium, with its vases of blooming fresh flowers, and you won't believe that this place is kin to Holiday Inn's assembly-line roadside staples. Its location is a nice surprise as well: east of the Magnificent Mile and close to the Ohio Street Beach and Navy Pier. Although the rooms are pretty basic, the amenities make this one of the best values in the city.Fitness devotees will rejoice because the Holiday Inn is located next door to the Lake Shore Athletic Club, where guests may enjoy the extensive facilities free of charge (including an indoor pool). The hotel also has its own spacious outdoor pool and sun deck. The views are excellent, especially looking north toward the Hancock Building and Monroe Harbor. You might want to splurge on one of the master suites, which boast large living-room areas with wet bars, along with a Jacuzzi-style tub and sauna in the bathroom.The Holiday Inn is a good bet for the budget-conscious family: Kids under 18 stay free in their parent's room, and those 12 and under eat free in the hotel's restaurants. Leave the pay-per-view movies one night and head to the massive new AMC theaters next door, where all 21 screens offer stadium seating.

W Chicago Lakeshore
The only hotel in Chicago with a location on the lake, this property prides itself on being a hip boutique hotel -- but sophisticated travelers might feel like it's trying way too hard with dance music playing in the lobby and the black-clad staff members doing their best to be eye candy. The compact rooms are decorated in deep red, black, and gray -- a scheme that might strike some travelers as gloomy. And although the Asian-inspired bathrooms are stylish, the wooden shades that separate them from the bedroom don't make for much privacy. In W-speak, rooms and suites are designated "wonderful" (meaning standard, with a city view) or "spectacular" (meaning a lake view, for which you'll pay more). I actually prefer the "wonderful" rooms with their dramatic city views. Of the few boutique hotels in Chicago, the W Lakeshore has the best location, within easy reach of outdoor activities (the beach, bike paths, and Navy Pier), restaurants, and nightlife -- just don't take the place too seriously.The W Lakeshore boasts Wave, a stylish internationally inspired seafood restaurant, and Whiskey Sky, the hotel's see-and-be-seen spot designed by Rande Gerber.

Crowne Plaza Chicago -- The Silversmith
You might call The Silversmith a hidden gem. The landmark building, designed by the celebrated firm of D. H. Burnham and Company, was built in 1897 to serve the jewelry and silver trade on Wabash Avenue, still known as Jeweler's Row. Rooms come in varying configurations, with 12-foot-high ceilings, 10-foot picture windows, Frank Lloyd Wright-inspired wrought-iron fixtures, armoires, and homey bedding; bathrooms are generously sized. Because buildings surround this very urban hotel, natural light is limited in the rooms; those along the hotel's main corridor tend to be quite dark. Rooms at the front on the fifth floor or higher have a quintessentially Chicago view: the El tracks along Wabash Avenue. Yes, the windows are extra-thick to muffle the noise of the rumbling trains, but you'll want to avoid the lower-level floors if you like things quiet. For the best combination of natural light and views, request a Wabash Avenue room on the 9th or 10th floor.Word about The Silversmith has been slow getting out (even Loop office workers who pass by it daily don't know it's there), so rooms don't book up as quickly as other, hotter spots. That's good news for thrifty travelers looking for deals (I hear the suites often get discounted). You also are more likely to find a room here during the busy convention season. Guest-friendly touches include an evening wine-and-cheese reception and complimentary desserts available at night in the lobby (including Eli's cheesecake, one of the city's signature sweet treats).