Situated in the heart of "the Loop," the contemporary Central Loop Hotel is steps from all of Chicago’s major business and cultural destinations such as Chicago ...
Central Loop Hotel$109Central Loop Hotel$109
Built in 1927, this Chicago hotel is one block from Michigan Avenue shopping and Rush Street restaurants and nightlife; Lake Michigan is within five blocks.
The Whitehall Hotel$94The Whitehall Hotel$94
This 39-story Chicago hotel is across the river from Magnificent Mile shopping, six blocks from Lake Michigan, and a half-mile from the Loop's theater district ...
Wyndham Grand Chicago Riverfront$119Wyndham Grand Chicago Riverfront$119
Situated near the airport, this hotel is 0.4 mi (0.6 km) from Allstate Arena and within 3 mi (5 km) of Rivers Casino and Donald E. Stephens Convention Center. ...
Edward Hotel Chicago$78Edward Hotel Chicago$78
Hotel Felix Chicago is 5 blocks from the Magnificent Mile, one of America’s most dazzling thoroughfares. It’s a 7-minute cab ride to the Navy Pier Ferris Wheel, ...
Hotel Felix Chicago$87Hotel Felix Chicago$87
Located in Near North Side, this luxury hotel is within a 10-minute walk of Tribune Tower and Wrigley Building. Navy Pier and Chicago Children's Museum are also ...
Loews Chicago Hotel$159Loews Chicago Hotel$159
The only hotel on airport property, the Hilton Chicago O'Hare Airport is located 2 miles from the Donald E. Stephens Convention Center and the Rosemont Theatre, ...
Hilton Chicago O'Hare Airport$93Hilton Chicago O'Hare Airport$93
This 1925 Beaux Arts-style Chicago hotel is steps from Millennium Park, 2 blocks from Macy's and the Art Institute, and 1 mile from Lake Michigan, Magnificent ...
Palmer House a Hilton Hotel$118Palmer House a Hilton Hotel$118
From food to theater and Lake Michigan to the Loop, Chicago is home to some equally big names. But you don't need to fly in on Obama's Air Force One or have pockets as deep as Oprah to be able to experience a Chicago vacation at its fullest. Take a stroll down the Magnificent Mile, catch a Cubs game at Wrigley Field, and soak up the waterfront culture of the Second City.
Before you rush to Millennium Park, allow CheapTickets to help you with the planning. We'll share the city's top highlights that will blow your mind -- without blowing your budget.
If you visit Chicago in the early fall you will experience the best of its weather as it retains its warm temperatures but loses the humidity of the summer months. Spring time is cooler, and it is a good time to capture those cheaper flights and hotels. The Chicago Blues Festival every June attracts headline acts from around the country and is extremely popular, as is the early three-day snow sculpturing exhibition held every winter on Navy Pier. Grant Park at the harbor hosts an annual Taste of Chicago Food Festival which, as you might expect, appeals to a wide audience.
Capture the history of Alta Vista Terrace close to Wrigley Field, modeled on a block of row houses in London.
Take lunch at the charming Cafe Selmarie overlooking the Lincoln Square Fountain and consume some mouth-watering cakes.
Walk the lake-front trail north towards Montrose Harbor with some incredible views of the city skyline.
Admire the Oriental architecture on a steady stroll through the pleasant and quiet surroundings of Ping Tom Memorial Park.
Dine out at Pancho Pistolas restaurant serving delicious Mexican cuisine in the Bridgeport neighborhood.
For an easy escape without having to spend a cent on your Chicago travels, take the afternoon to meander through the menagerie at the Lincoln Park Zoo. Not only is it brimming with wildlife exhibits and beautiful historical architecture, it's totally free and open 365 days a year.
The Mag Mile is a revered for its incredible shopping and eating scene, as well as the festivities that occur throughout the year. Lined by colorful tulips in the springtime and glittering lights during the holidays, the Mag Mile is chockablock with department stores and notable landmarks, from the Wrigley Building to Oak Street Beach. For incredible views on your Chicago travels, head to the Hancock Observatory or spend a few bucks on a cocktail in the Signature Lounge.
If you want to experience the cultural side of the Second City on your Chicago vacation, make a beeline for the Chicago Cultural Center where admission is free. After taking in the impressive architecture and stunning Tiffany dome, head to the Art Institute across the street to view the amazing collection of Impressionist art and the new Modern Wing. Take a stroll to the Buckingham Fountain and laze in the sun, or take in a nighttime light show.
For a bustling carnival vibe along Lake Michigan, wander along the Navy Pier promenade and catch the spirit of Chicago. Bring the kids to the Children's Museum, Shakespeare Theatre or Stained Glass Gallery, and marvel at the incredible skyline views from the 150-foot Ferris wheel. Grab a bite to eat at Chicago institution Harry Caray's, and rest your weary feet to enjoy the free weekly fireworks.
Chicago has plenty of parks, but this one is worth a special mention. An impressive feat of engineering, landscaping and cultural celebration, Millennium Park is home to the iconic Cloud Gate sculpture and splashy Crown Fountain video sculpture. Enjoy a concert at Jay Pritzker Pavilion, the go-to spot for the best in outdoor entertainment.
* 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.