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7800 Travelers rated Chicago highly for Urban and Skyscrapers

Book a package and join the 188 others who’ve received 100% off their flights this year!
Book a package and join the 188 others who’ve received 100% off their flights this year!
Book a package and join the 188 others who’ve received 100% off their flights this year!
Book a package and join the 188 others who’ve received 100% off their flights this year!

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Featured Chicago Flight + Hotel packages

2 to 5 night Chicago trip packages

Top Rated Chicago Hotels

Estimated price for 1 night/2 adults

Hotel Essex Chicago
Hotel Essex Chicago
4.0 out of 5.0 800 S Michigan Ave, Chicago, IL
Free Cancellation
$90
4.5/5 (10 reviews)

The property has a great location, close to downtown proper but good for drivers. I highly recommend valet parking because the self-park lots nearby do not look safe and the reviews I've read show undesirable information. The hotel rooms are a decent 4 star experience, however, the noise from the ...

Reviewed on May 19, 2019
Omni Chicago Suites - Magnificent Mile
Omni Chicago Suites - Magnificent Mile
4.5 out of 5.0 676 N Michigan Ave, Chicago, IL
Free Cancellation
$179
4.4/5 (72 reviews)

Staff was great and always friendly. Hotel on the older side and rooms could use some updating but overall very clean and spacious. Would have been better if WiFi was free.

Reviewed on Apr 25, 2019
Hyatt Centric Chicago Magnificent Mile
Hyatt Centric Chicago Magnificent Mile
4.0 out of 5.0 633 N Saint Clair St, Chicago, IL
Free Cancellation
$140
4.2/5 (319 reviews)

Great location, walking distance for shopping and dining. Hotel is clean and staff is very accommodating.

Reviewed on Mar 10, 2019
Hyatt Regency Chicago
Hyatt Regency Chicago
4.0 out of 5.0 151 East Wacker Dr, Chicago, IL
Free Cancellation
$159
4.2/5 (914 reviews)

Great location downtown. A little confusing with the different towers and entrances. Almost missed our Go Express pick-up

Reviewed on May 15, 2019
Embassy Suites Chicago Downtown Magnificent Mile
Embassy Suites Chicago Downtown Magnificent Mile
4.0 out of 5.0 511 North Columbus Drive, Chicago, IL
Free Cancellation
$153
4.1/5 (407 reviews)

Great location. Morning complimentary breakfast was exceptional with a chef preparing eggs to order 5:30 complimentary cocktails and snacks was a big surprise. Would definitely stay there again on my next visit to Chicago!

Reviewed on May 16, 2019
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4.0 out of 5.0 17 E Monroe St, Chicago, IL
Free Cancellation
$125
4.1/5 (896 reviews)

No complaints. Great location, friendly staff and the building has alot on character.

Reviewed on May 13, 2019

Cheap Chicago Hotels

Estimated price for 1 night/2 adults

Freehand Chicago
Freehand Chicago
3.5 out of 5.0 19 East Ohio Street, Chicago, IL
Free Cancellation
$108
4.0/5 (76 reviews)

There is mold in the shower but overall the room was fine.

Reviewed on Apr 29, 2019
BudgetBarDining
Motel 6 Elk Grove Village - O'Hare
Motel 6 Elk Grove Village - O'Hare
2.0 out of 5.0 2881 Touhy Ave, Elk Grove Village, IL
Free Cancellation
$45
3.6/5 (68 reviews)

Friendly staff. Complimentary airport shuttle was great.

Reviewed on May 25, 2019
BudgetTransportation ServicesAirport Transportation
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago
2.0 out of 5.0 65 E Harrison St, Chicago, IL
Free Cancellation
$125
3.0/5 (376 reviews)

It was a nice basic place with very comfortable beds and good WiFi.

Reviewed on May 21, 2019
BudgetDiningFree Wifi

Things to do in Chicago

See all 145 things to do in Chicago

Things to do in Chicago

Art Institute of Chicago

Housing more than 300,000 works of art, this Michigan Avenue gem spans centuries' worth of masterpieces, from the "A Sunday on La Grande Jatte" by Seurat and "American Gothic" by Grant Wood. A 2009 expansion enhanced the appeal thanks to the super sleek Modern Wing designed by Pritzker Prize–winning architect Renzo Piano.

The Ryan's Education Center invites the tykes to engage in their environment with interactive exhibits. Organic restaurant Terzo Plano fuels the romance with glorious views of the Pritzker Pavilion.

The Signature Lounge at the John Hancock

Take the elevator up 96 flights to soak in the views from the Signature Lounge, the best seat in Chicago. While there is no admission fee, expect pricy cocktails -- but paired with floor-to-ceiling panoramas of the Windy City, they're worth it.

If time permits, opt for the Sunday brunch or a special occasion dinner at the Signature Room, equally dazzling with oversized windows and an impressive wine list.

Second City

If the careers of John Belushi, Gilda Radner, Tina Fey, Mike Meyers and Steve Carrell have proven anything, it's that a stop at Second City could help rocket a career. The talent incubator in the heart of Old Town hosts both sketch-based and improv performances in an intimate setting.

Navy Pier

Expect to feel like a kid again throughout the lakeside treat, which boasts a Ferris wheel, the Chicago Children's Museum, Chicago Shakespeare Theater, bikes for rent, boat rides, miniature golf and headlining acts such as Cirque Shanghai Extreme.

Come summertime, pull up a chair at an al fresco restaurant -- Harry Caray's is a favorite -- to watch the twice-weekly fireworks.

Wrigley Field

No curse can deny Chicago's unwavering love for the Cubs -- and it's as much about the scene as it is about the fantasy of winning a World Series. And it doesn't get any more Chicagoan than seeing fans swig beers during a rowsing rendition of "Take Me Out to the Ball Game," or cheering from the rooftop decks in Wrigleyville. Expect as much flavor surrounding the stadium, as diehards continue the party along Clark, Addison and Waveland.

Millennium Park

Home to Cloud Gate, Crown Fountain, the Jay Pritzker Pavilion and more attractions, the park leaves visitors impressed by striking landmarks, lake access and buzz from the neighboring Magnificent Mile.

The best part: Many summer activities are free, including outdoor yoga and Pilates, Chicago SummerDance, and the Family Fun Festival at Chase Promenade North.

Willis Tower

Its name may have changed, but in the hearts of Chicagoans, Willis Tower will always be Sears Tower. The building soars 110 stories above the Windy City, and is home to the world's tallest green roof on the 90th floor. The Skydeck invites visitors to look down at the metropolis via clear ledges, but only if you dare.

Buddy Guy's Legends

Chicago never sounded so sweet than at this iconic blues den in the South Loop. The stage jams seven nights a week – with heavy hitters such as Eric Clapton and John Mayer among the past featured acts.

For a side of Cajun spice to go with your blues, order from a menu of Southern classics, including okra, gumbo and jambalaya.

Lakefront Trail

Chicago is blessed with an 18.5-mile path along the shores of Lake Michigan, a stretch bustling with bikers, runners, soccer fields, beaches and parks. Connecting neighborhoods as far south as the South Shore to as far north as Edgewater, the path is an easy way to combine sightseeing with recreation.

Insider tips for Chicago travel

Alinea

If you're planning to visit this famous restaurant, book your reservation at least two months in advance. If you do score a table, don't be discouraged if you can't spot the restaurant immediately. It's in a grey brick storefront with no sign.

Cocktails

Looking for an offbeat place for cocktails in one of Chicago's hippest neighborhoods? Consider the Bedford in Wicker Park, located in a former bank building. Imbibe old-school cocktails in the actual vault, which is dotted by safe deposit boxes.

Boat tours

For a leisurely lesson on Chicago's architecture, catch a boat cruise from Navy Pier or at the bottom of the Wrigley Building.

*Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2018 to December 31, 2018 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.

* Prices reflect the lowest "base rate" found over the next 30 days. Rates are subject to change and may not include taxes and fees, hotel service charges, extra person charges, or incidentals, such as room service. All rates are displayed in USD unless otherwise noted. Converted rates are provided for your convenience. They are based on today's exchange rate, but the hotel will charge you in the local currency.