Cheap Chicago Vacations

Chicago

Your Chicago vacation

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.

Cheap Vacation Packages

Cheap Chicago Vacation Packages

The Talbott Hotel

4 stars
4.6 / 5 1213 reviews
Independently-owned and with a dedication to green practices, The Talbott Hotel has been a fixture in Chicago's Gold Coast neighborhood since 1927. The hotel mingles old-world sophistication with modern conveniences - the lobby has a cozy, open-fire warmth and the vintage-style boardrooms feature 1920s mahogany walls. Awarded the Best in Stay Award in 2014 - 2015, the Talbott features exclusive touches like the creative Tippling Brothers cocktail menu at the Mercadito Fish Co., and the knowledgeable 'Concierge Blog' on the hotel's site, setting the hotel far apart from other Chicago accommodations. Key facts149 guestroomsPets allowed (up to 50 pounds, and fees may apply)Conference and event spaces: 3 rooms, up to 200 guestsFitness centerLaundry serviceFree Wi-Fi Restaurant/bar: Mercadito Fish Co. NeighborhoodWith a prime location just a few blocks from Washington Square Park, Oak Street and the Magnificent Mile, The Talbott Hotel comes with easy access to shops like Bloomingdale's and Macy's, as well as the scenic Lakefront Trail on the shores of Lake Michigan. The Art Institute of Chicago is less than two miles from The Talbott's front entrance, boasting a staggering collection of over 250,000 works of art, including work by Vincent van Gogh, Claude Monet and Mary Cassatt. Hints and tipsFor privileged views of Chicago and a bit of distance from busy Delaware Street, ask for a room on the upper floors.For a more personalized stay, the Talbott Hotel's packages offer everything from the princess treatment for young daughters - including milk and cupcakes at turndown - to a $50 gift certificate  for the 900 North Michigan Shops.
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Nightly rates from $116

Hilton Garden Inn Chicago Downtown North

3 stars
4.0 / 5 105 reviews
Business and leisure hotel with free Wi-Fi near the Magnificent Mile Business and leisure travelers target this Streeterville hotel for its proximity to the Magnificent Mile, only a few blocks away. The three-star Hilton Garden Inn Chicago covers all the basics: well-kept rooms, complimentary Wi-Fi throughout and a place to dine. Weber Grill of backyard barbecue fame invites diners to sample its signature charcoal fired steaks, burgers and chicken. Other must-sees aren't far away, like the family-friendly Navy Pier, the Loop, the Financial District and McCormick Place. Highlights Free Wi-Fi in the lobby and roomsSkylit indoor pool and JacuzziClose to the Magnificent Mile, Navy Pier and other classic Chicago gems7,000 square feet of meeting space RoomsRooms at Hilton Garden Inn are 300 square feet, configured with a large king or two queen beds, all of which feature the Garden Sleep System. For added comfort, each room includes a comfortable chair and ottoman, generous work desk and Herman Miller chair, flat-screen TV, individual climate control, microwave, refrigerator and complimentary high-speed Internet access. Guests who prefer rooms with a skyline view can make the request at check-in. FeaturesIf a hotel's priority is to create a second, albeit temporary home for guests, then visitors at the Hilton Garden Inn Chicago Downtown North will be pleased. In addition to a business center and classic American restaurant (Weber Grill), the hotel provides an ATM, a 24-hour pantry for sundries, laundry and valet service and car rental services. Oh, and don't forget to pick up free cookies between 5 p.m. and 7 p.m. Transportation O'Hare International Airport (16 mi/25.8 km)Midway Airport (12 mi/19.3 km)Closest train stops: Blue Line (Jackson to O'Hare) and Orange Line (State/Lake to Midway)McCormick Place Convention Center (2.8 mi/4.5 km) Attractions  Magnificent Mile River NorthNavy PierMuseum of Contemporary ArtMillennium Park Grant ParkShedd AquariumAdler Planetarium Business 7,000 square feet of function space on the 12th floor with views of the Chicago skylineBusiness center with computers, copier, fax machines and printersConference services staff and audiovisual team Policies & feesThe pool is closed for renovation. Guests can use the pool across the street at the sister hotel Embassy Suites by Hilton. Hilton Garden Inn apologizes for any inconvenience this may cause.
Value Complimentary wired and Wi-Fi Internet Access
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Nightly rates from $89

Inn of Chicago, an Ascend Collection hotel

3 stars
3.3 / 5 235 reviews
Contemporary style, European charm in ChicagoIn the Roaring '20s, this boutique Streeterville hotel hosted celebrities and showgirls. While those times have faded, the air of glamour remains at the Inn of Chicago, an Ascend Collection hotel. For proof, just stroll the lobby, where zebra ottomans, fresh-cut orchids and metallic embossed walls create drama and urban appeal. With its central location and focus on value, the Inn of Chicago is a gem for business or leisure travelers seeking convenient access to the Magnificent Mile and its many diversions. Highlights Prime Chicago location just east of Magnificent MileFree high-speed wireless Internet accessComplimentary stay for children under 18The 22nd floor Skyline Terrace RoomsThe rooms and suites at the Inn of Chicago feel more like apartments than hotel rooms, and that’s on purpose. Back in the 1920s, the former Hotel St. Clair offered one-bedroom apartments, and the effects linger today at the Inn of Chicago. Space for entertaining, working and lounging are separate from the sleeping area. Big picture windows with skyline views, photos of Chicago, zebra upholstery and unique layouts lend to a chic city vibe. FeaturesGreat city views might well be the most valuable cache for Chicago hotels and for the Inn of Chicago, this view comes at the Skyline Terrace on the 22nd floor. The Sky Suites also provide lofty views, while a dedicated party space accommodates up to 100 guests for weddings and other social events. Transportation O’Hare International Airport (15.6 mi/25.1 km) Midway Airport (9.8 mi/15.9 km) Blue Line (Grand) (1.7mi/2.7 km) Orange Line (State/Lake) (0.5 mi/0.9 km) McCormick Place Convention Center (2.9 mi/4.6 km) Attractions The Magnificent Mile (0.1 mi/0.1 km) Water Tower Place (0.4 mi/0.6 km) Navy Pier (1 mi/1.6 km) Lake Michigan (0.2 mi/0.3 km) Millennium Park (0.7 mi/1.1 km) Business Business center work station 5 meeting rooms 5,500 square feet of function space for up to 125 guests Complimentary wireless Internet access Concierge services Policies and fees NOTE: Parking fees are as follows: $48 for self-parking and $52 for valet parking with unlimited in/out privileges.
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Nightly rates from $60

Warwick Allerton Hotel Chicago

4 stars
4.0 / 5 602 reviews
As one of the first high-rises to grace Chicago's fashionable Michigan Avenue, the Warwick Allerton Hotel Chicago became synonymous with high style, luxurious hotel accommodations and impeccable service. Today, the hotel has kept the commitment to treat every guest like a celebrity and continues to make each stay at the Warwick Allerton Hotel Chicago as comfortable and rewarding as their predecessors did more than 80 years ago. Of all Magnificent Mile Chicago hotels, Warwick Allerton Hotel Chicago's historic Italian Renaissance style will dazzle you. The 443 guest rooms, including 84 suites, are perfect for your next Chicago meeting, banquet or wedding. The Warwick Allerton Hotel Chicago offers a variety of impressive, natural lit meeting rooms able to accommodate your group of 10 to 200. The Renaissance Ballroom located on the 23rd floor offers a stunning view of Michigan Avenue and Downtown Chicago. If you are looking for a luxury hotel in downtown Chicago, stay with us and experience our exquisite service and our great location. Welcome to the Warwick Allerton Hotel Chicago! Overnight valet parking $60 effective July 1st, 2013 A valid credit card must be presented at check-in for incidental charges.
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Nightly rates from $79

Congress Plaza Hotel at Grant Park

3 stars
3.3 / 5 1130 reviews
With its neon-red sign standing out against the Chicago skyline, its vaulted Italianate ceilings, and glimmering 'Gold Room' banquet hall, the Congress Plaza Hotel makes an imposing first impression. Once known as the "Home of Presidents" due to its popularity with both Roosevelt's, Woodrow Wilson and Richard Nixon, it's been operating since 1893. Valet dry-cleaning and barber services of yesteryear sit side-by-side with modern amenities like audiovisual tech for business meetings and a 24-hour fitness center. On-site eating options are globally diverse (Rafael's Steakhouse) and come straight from the griddle in the morning (Gazebo Restaurant). In the evenings, settle into a leather back armchair with a bourbon, or take your shots at the dartboard in the Congress Lounge, where both business users and vacationers gather for some much-needed R&R. Key facts871 guestrooms36 suites23 meeting/event rooms2 restaurants: Rafael's Steakhouse, Gazebo RestaurantCongress Lounge & BarGift shopBarber shop24-hour gymValet dry cleaning/shoeshineSmoking rooms available on request NeighborhoodAcross the street from Grant Park and the famous Buckingham Fountain, Congress Plaza rests on the main thoroughfare and shopping mecca of Michigan Avenue, aka, the Magnificent Mile. The hotel is walking distance from world-renowned institutions like the Art Institute of Chicago, Shedd Aquarium, and the fascinating Field Museum. Found on the banks of Lake Michigan, the Field Museum is the home of "Sue," the largest and most complete Tyrannosaurus Rex skeleton ever discovered, as well as a life-size Maori meeting house. Hints and tipsThe Congress is frequently nicknamed 'the most haunted hotel in Chicago,' and budding paranormal detectives should request a room in the oldest part of the building, the South Tower, for the 'highest chance' of ghostly activity.Be on the lookout for characters like notorious murder victim Peg Leg Johnny, or test your courage near the 12th floor room which was allegedly closed down due to paranormal activity.
Value Winter Sale - Save 20%
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Nightly rates from $79
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Cheap Flights
Departure Arrival Travel dates Round-trip
New York Chicago Thu, Dec 4 - Tue, Dec 9 $147
Los Angeles Chicago Tue, Jan 6 - Wed, Jan 7 $184
Washington DC Chicago Sat, Dec 6 - Wed, Dec 10 $52
San Francisco Chicago Mon, Dec 8 - Wed, Dec 10 $259
Newark Chicago Mon, Dec 15 - Fri, Dec 19 $239
Atlanta Chicago Fri, Dec 5 - Tue, Dec 9 $82
Seattle Chicago Mon, Dec 8 - Tue, Dec 9 $252
Boston Chicago Wed, Dec 10 - Sun, Dec 14 $201
Dallas Chicago Sat, Jan 17 - Tue, Jan 27 $107
Denver Chicago Wed, Dec 10 - Mon, Dec 15 $95
Phoenix Chicago Tue, Dec 2 - Mon, Dec 8 $152
Orlando Chicago Wed, Jan 7 - Tue, Jan 13 $145
San Juan Chicago Thu, Jan 15 - Thu, Jan 22 $332
Mexico City Chicago Tue, Jan 13 - Wed, Feb 4 $431
Philadelphia Chicago Mon, Jan 12 - Tue, Jan 13 $277
San Diego Chicago Wed, Jan 14 - Mon, Jan 19 $241
Fort Lauderdale Chicago Wed, Dec 3 - Wed, Dec 10 $182
Las Vegas Chicago Tue, Dec 23 - Tue, Jan 6 $186
Guadalajara Chicago Thu, Jan 15 - Sat, Jan 31 $502
Tampa Chicago Sat, Dec 20 - Mon, Jan 5 $122
Houston Chicago Thu, Dec 18 - Tue, Jan 13 $155
Baltimore Chicago Sat, Dec 13 - Tue, Dec 16 $157
Honolulu Chicago Fri, Dec 5 - Fri, Dec 12 $737
Orange County Chicago Thu, Jan 22 - Thu, Jan 29 $266
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Best time to take a vacation to Chicago

  • 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.

Insider tips for Chicago travel

  • Pancho Pistolas

    Dine out at Pancho Pistolas restaurant serving delicious Mexican cuisine in the Bridgeport neighborhood.

  • Ping Tom Memorial Park

    Admire the Oriental architecture on a steady stroll through the pleasant and quiet surroundings of Ping Tom Memorial Park.

  • Montrose Harbor

    Walk the lake-front trail north towards Montrose Harbor with some incredible views of the city skyline.

  • Alta Vista Terrace

    Capture the history of Alta Vista Terrace close to Wrigley Field, modeled on a block of row houses in London.

  • Cafe Selmarie

    Take lunch at the charming Cafe Selmarie overlooking the Lincoln Square Fountain and consume some mouth-watering cakes.

Chicago highlights

  • Chicago highlights
  • Navy Pier

    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.

  • Magnificent Mile

    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.

  • Lincoln Park Zoo

    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.

  • Cultural Chicago

    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.

  • Millennium Park

    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.

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