Orbitz is pleased to offer airline tickets on United Airlines, which operates 3 regularly scheduled daily non-stop flights from Portland (PWM) to Chicago (ORD), departing between 6:45am and 5:23pm. Usually a Canadair Regional Jet 700 is flown for this route. The average travel time from Portland, ME to Chicago, IL is 2 hours and 46 minutes.

Quick Flight Searches
Weekend Trips - Search
Upcoming weekend flight specials and airline deals on flights to Chicago (ORD) from Portland (PWM) Weekend travel in February from PWM to ORD Weekend travel in March from PWM to ORD Weekend travel in April from PWM to ORD Vice versa? Search for last minute deals on airline tickets from Chicago (ORD) to Portland (PWM) Weekend travel in February from ORD to PWM Weekend travel in March from ORD to PWM Weekend travel in April from ORD to PWM
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 Portland to Chicago

Regularly Scheduled Flights to Chicago (ORD) from Portland (PWM)
				Daily Non-Stops		Select Non-Stop		Earliest Flight		Last Flight
	United Airlines			3		-		6:45am		5:23pm
	All Nippon Airways			1		-		6:42am		6:42am

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

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).

Jane Addams Hull-House Museum
Three years after the Haymarket Riot, a young woman named Jane Addams bought an old mansion on Halsted Street that had been built in 1856 as a "country home" but was now surrounded by the shanties of the immigrant poor. Here, Addams and her co-worker, Ellen Gates Starr, launched the American settlement-house movement with the establishment of Hull House, an institution that endured on this site in Chicago until 1963. (It continues today as a decentralized social-service agency known as Hull House Association.) In that year, all but two of the settlement's 13 buildings, along with the entire residential neighborhood in its immediate vicinity, were demolished to make room for the new University of Illinois at Chicago campus, which now owns the museum buildings. Of the original settlement, what remain today are the Hull-House Museum, the mansion itself, and the residents' dining hall, snuggled among the ultramodern, poured-concrete buildings of the university campus. Inside are the original furnishings, Jane Addams's office, and numerous settlement maps and photographs. Rotating exhibits re-create the history of the settlement and the work of its residents, showing how Addams was able to help transform the dismal streets around her into stable inner-city environments worth fighting over. Allow a half-hour.

Spertus Museum
The Spertus Museum, an extension of the Spertus Institute of Jewish Studies, showcases intricately crafted and historic Jewish ceremonial objects, textiles, coins, paintings, and sculpture, tracing 5,000 years of Jewish heritage. Though small in scale, the Zell Holocaust Memorial exhibit is particularly moving, featuring a video montage of Holocaust victims with a Chicago connection and a display of related artifacts and documents. The kid-oriented Artifact Center is a re-creation of a Middle Eastern archaeological dig, where children can search for buried treasures (reserved for school groups in the mornings, it's open to the public in the afternoon). The institute's Asher Library boasts one of the largest collections of Jewish books, periodicals, videos, and music in the country. The Bariff Shop for Judaica carries a large selection of art, books, music, videos, and contemporary and traditional Jewish ceremonial gifts. Allow 1 hour.

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

Fairmont Hotel
The Fairmont is easily one of the city's most luxurious hotels, offering an array of deluxe amenities and services and regularly hosting high-level politicians and high-profile fundraisers. Open since the mid-1980s, its overall effect is chic but a bit impersonal. The entrance faces anonymous office towers, and you're likely to wander the circular lobby awhile before finding the check-in desk. Still, the rooms are large and decorated in a comfortable, upscale style (ask for one with a lake view, although city-view rooms aren't bad either). The posh bathrooms feature extra-large tubs, separate vanity areas, and swivel TVs. The windows open (a rarity in high-rise hotels), so you can enjoy the breeze drifting off Lake Michigan. Suites have one or two bedrooms, a living room, a dining area, and a built-in bar -- and all come with lake views. The hotel is connected to the city's underground "pedway" system, through which you can walk all the way to Marshall Field's on State Street -- a bonus on inclement days (a florist, pharmacy, and salon are conveniently located in an adjoining building).Facilities: Restaurant (American/eclectic); lounge; access to Lakeshore Athletic Club, one of the top health clubs in the city (with full-court basketball, climbing wall, pool, and spa); concierge; business center; 24-hr. room service; babysitting; laundry service; 24-hr. dry cleaning.

Hotel Monaco
This 14-story boutique hotel may try a little too hard to be "fun": Guests are greeted by derby-hatted doormen, funky house music plays in the lobby, and you can even request a goldfish with its own name to swim about a fishbowl in your room. But it offers an upbeat alternative to the many cookie-cutter business hotels in the city. The plush, jewel-toned, 1930s-inspired decor makes the sizeable rooms resemble theatrical set pieces. The eclectic furnishings include armoires, mahogany writing desks, and plush beds; suites come with a two-person whirlpool spa and CD player. Rooms on the top three floors have views of the Chicago River and surrounding skyscrapers. Given the hotel's playful spirit, it attracts a younger clientele, with an overall vibe that is laid-back and friendly rather than so-hip-it-hurts (this is Chicago, after all, not New York).

Tremont Hotel
The Tremont won't dazzle you with style or amenities, but it fits the bill for anyone looking for a small, European-style hotel. The cozy lobby (complete with fireplace) makes a fine space to hang out and plan your itinerary for the day. The guest rooms aren't too big -- there's space for a bed, a desk, and either a sofa or two chairs -- but they are cheery, with yellow walls and large windows. Ask for a room facing Delaware Street if you crave natural light (rooms in other parts of the hotel look into neighboring buildings). The furniture shows signs of wear, and the bathrooms are fairly basic, but the Tremont will appeal to anyone who likes their hotels homey rather than slick.The steak-and-chops restaurant off the lobby, the memorabilia-filled Mike Ditka's Restaurant, is co-owned by the legendary former Chicago Bears football coach.