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 Silversmith Hotel Chicago

3 stars
4.2 / 5 238 reviews
Landmark in the Loop near attractions and shoppingIt's only fitting that this historic hotel is just a few blocks from Jewelers Row given its name and former purpose. In the 1890s, its tenants worked in the jewelry and silver trade. Today, landmark elements -- a cast iron staircase, terra cotta touches -- give the Silversmith Hotel Chicago a unique architectural identity. Ideally situated near the Magnificent Mile and Millennium Park, the Silversmith Hotel Chicago appeals to budget-minded travelers seeking quick access to Chicago's most popular attractions. Highlights One block to the Magnificent Mile, Millennium Park and State Street shopping24-hour fitness centerFree high-speed Internet access throughout the hotelDining at Ada's Deli & Restaurant and cocktails at the 14 Karat LoungeHistoric, independent hotel with Arts and Crafts style RoomsRooms and suites at the Silversmith Hotel Chicago serve their purpose, providing comfortable beds and a place to freshen up in between sightseeing excursions. The hotel’s 12-foot ceilings add dimension, while 10-foot picture windows view the city and the El. Wood headboards, desks and Prairie-style lamps complete the casual look. Complimentary wireless Internet access is available throughout the property. FeaturesIntimate and under the radar, the Silversmith Hotel Chicago does not fit the trendy boutique mold, but guests will appreciate its location. No less than a dozen attractions are within walking distance, including the theater district, Jewelers Row, State Street, Grant Park and Millennium Park. Transportation O'Hare International Airport (15.8 mi/25.4 km)Chicago Midway Airport (9.2 mi/17.8 km)Blue Line (Monroe/Dearborn to O'Hare) (0.2 mi/0.3 km)Orange Line (Madison/Wabash to Midway) (0.1 mi/0.1 km)McCormick Place Convention Center (2.1 mi/3.5 km) Attractions Jewelers Row (0.1 mi/0.1 km)The Art Institute of Chicago (0.1 mi/0.1 km)Millennium Park (0.3 mi/0.4 km)Grant Park (0.4 mi/0.6 km)State Street (0.6 mi/0.9 km)Field Museum (1.2 mi/1.9 km)Shedd Aquarium (1.2 mi/1.9 km)Adler Planetarium (1.5 mi/2.3 km) Business Executive boardroom hosts up to 12 guestsChicago Landmark Room hosts up to 120 guestsPresentation equipment available, including 34-mm slide projector, flip chart and markers, LCD projector, microphone, VCR, overhead projector, modem lines and white boardsBusiness centerFree high-speed Internet access available throughout the Silversmith Hotel Chicago
Value Business Advantage - Arrival Day Cancel
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Nightly rates from $139

Inn of Chicago, an Ascend Collection hotel

3 stars
3.4 / 5 260 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, Inn of Chicago, an Ascend Collection hotel 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 wireless Internet access in the lobbyComplimentary stay for children under 18The 22nd floor Skyline Terrace RoomsThe rooms and suites at Inn of Chicago, an Ascend Collection hotel 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, an Ascend Collection hotel. 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. In-room wireless Internet access is available for a fee. FeaturesGreat city views might well be the most valuable cache for Chicago hotels and for Inn of Chicago, an Ascend Collection hotel, 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 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 $75

The Talbott Hotel

4 stars
4.6 / 5 1277 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. Policies and feesGuests must be at least 21 years of age to check in.
Value Last Minute Deal!
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Nightly rates from $148

The Godfrey Hotel Chicago

4 stars
4.4 / 5 115 reviews
Godfrey means peace and welcome; welcome to The Godfrey Hotel Chicago. The Godfrey Hotel Chicago offers unforgettable style from the Cubist-influenced facade to the chic accommodations, each detail of this striking new hotel has been designed with the guest's experience in mind.
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Nightly rates from $99

dana hotel and spa

4 stars
4.2 / 5 236 reviews
Modern retreat for healthy living in downtown ChicagoThe dana hotel and spa in Chicago's River North neighborhood balances the beauty of natural elements with the latest technology to create a modern retreat for healthy living. From the progressive health center to the Zeppelin MP3 media system in each room, the dana's core philosophy of wellness and individuality is expressed in all elements of the hotel. Bathed in natural light, the dana is an oasis of serene relaxation in a bustling city. Highlights Sweeping views at Vertigo Sky LoungeSpa at dana and 24-hour fitness centerEnjoy American favorites with a global twist at freestyle food + drink RoomsSleekly decorated with hints of Asian influence, standard rooms at the dana hotel and spa feature a half wall of floor-to-ceiling windows and walkout balconies. Serenity is infused in everything from the natural, sustainable floors to the 300-thread count Egyptian cotton sheets over pillow-top mattresses. Glass separates bath from boudoir and illuminates the shower rooms, featuring Italian rain shower fixtures and handcrafted tiles. FeaturesWith its mantra “the pleasure of giving,” the dana hotel and spa sets out to deliver a unique experience to its visitors. The spa offers an extensive array of treatments, from prenatal massages and organic manicures to customized facials and Italian mud body wraps. The focus on wellness continues through the high-tech fitness center, which is outfitted with Italian TechnoGym Kinetic Equipment to promote fluid motion. Vertigo Sky Lounge is Chicago’s premiere year-round indoor/outdoor lounge. With the dramatic city skyline as a backdrop, Vertigo is the ideal place to mix it up after work or into the night. It features a dancing fire pit, lush modern furnishings, craft cocktails and happy hour menus. New this summer is the Bartender’s Booth, where patrons can sample craft cocktails and off-menu bites while engaging with their very own mixologist.Guests can also head to freestyle food + drink on site to sample American favorites with a global twist during breakfast, lunch, dinner, and happy hour. The restaurant also has a street-side patio for outdoor dining (as weather permits). TransportationO’Hare International Airport (15.3 mi/24.7 km)Midway Airport (9.7 mi/15.7 km)Blue Line (Jackson/Lake) (1.1 mi/1.8 km)Orange Line (Chicago/Lake) (0.9 mi/1.5 km)McCormick Place Convention Center (3 mi/4.9 km) AttractionsMichigan Avenue (0.2 mi/0.3 km)Magnificent Mile (0.2 mi/0.4 km)Wrigley Building (0.4 mi/0.6 km)Tribune Tower (0.4 mi/0.6 km)Merchandise Mart (0.6 mi/0.9 km)Oak Street Beach (0.7 mi/1.1 km)The Loop (0.9 mi/1.5 km)Art Institute of Chicago (0.9 mi/1.5 km)Willis (Sears) Tower (1.1 mi/1.8 km)Navy Pier (1.3 mi/2 km) BusinessFully equipped business centerMeeting rooms with floor-to-ceiling windows, high-speed Internet access and audio/visual equipment Policies and Fees Overnight parking charge is $39 per night plus tax and unlimited in/out privileges
Value 12 Hour Sale - Save 20%!
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Nightly rates from $111
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Cheap Flights
Departure Arrival Travel dates Round-trip
New York Chicago Tue, Apr 7 - Sat, Apr 11 $97
Los Angeles Chicago Wed, Apr 15 - Mon, Apr 20 $158
Washington DC Chicago Wed, Mar 18 - Wed, Mar 25 $122
San Francisco Chicago Tue, Mar 31 - Mon, Apr 6 $246
Newark Chicago Sun, Apr 26 - Wed, Apr 29 $177
Atlanta Chicago Wed, Mar 11 - Wed, Mar 18 $98
Seattle Chicago Mon, Mar 23 - Wed, Mar 25 $272
Boston Chicago Sat, Mar 21 - Wed, Mar 25 $161
Dallas Chicago Tue, Mar 24 - Tue, Apr 7 $81
Denver Chicago Wed, Apr 1 - Wed, Apr 8 $97
Phoenix Chicago Wed, Apr 22 - Tue, Apr 28 $98
Orlando Chicago Wed, Mar 25 - Tue, Mar 31 $145
San Juan Chicago Tue, Apr 14 - Tue, May 12 $353
Mexico City Chicago Mon, Apr 6 - Fri, Apr 10 $349
Philadelphia Chicago Tue, Apr 14 - Wed, Apr 15 $98
San Diego Chicago Wed, Apr 22 - Tue, Apr 28 $219
Fort Lauderdale Chicago Thu, Mar 12 - Tue, Mar 17 $199
Las Vegas Chicago Wed, Apr 22 - Tue, Apr 28 $159
Guadalajara Chicago Wed, Mar 25 - Wed, Apr 15 $409
Tampa Chicago Thu, Mar 12 - Tue, Mar 17 $155
Houston Chicago Tue, Apr 7 - Mon, Apr 13 $95
Baltimore Chicago Tue, Apr 14 - Thu, Apr 16 $167
Honolulu Chicago Wed, Mar 4 - Mon, Mar 9 $707
Orange County Chicago Wed, Apr 15 - Wed, Apr 22 $257
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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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