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

Chicago's Essex Inn

3 stars
3.7 / 5 245 reviews
Affordable hotel south of Chicago's bustling downtown areaChicago's Essex Inn has an ideal location ideal on Michigan Avenue, just a few blocks south of the more congested areas of downtown Chicago. Grant Park is across the street, along with many famous Chicago attractions, including Millennium Park and the Art Institute. Sleek in design, the Essex Inn boasts a metal and glass lobby, floor-to-ceiling windows with city views and an impressive atrium housing a large pool. ADA-compliant areas are also available at Chicago's Essex Inn. Highlights Great value in the city for its location and amenitiesRooftop pool available year-roundLarge, well-equipped fitness room overlooks pool deck RoomsA color palette grounded in rich orange and brown earth tones keeps the scene warm. Floor-to-ceiling windows play up the hotel’s strongest asset, the city views. Flat-screen TVs and refrigerators are standard amenities in each room at Chicago's Essex Inn. Guests can have complimentary access to wireless Internet. Rooms also feature ADA-compliant areas. FeaturesIn a metropolis like Chicago, pools and green space are precious real estate. Chicago's Essex Inn has both. The garden pool feels like a competitive swimming complex, with a retractable atrium and global flags hanging from the rafters. The pool area features large windows that look out onto the well-manicured grounds of the rooftop garden. From the garden, guests enjoy skyline views of Grant Park and Lake Michigan from comfortable patio chairs and tables. Next to the pool is a large fitness center, featuring bikes, treadmills, weight machines, free weights, as well as six TVs.Visitors to Chicago who have come to sightsee take advantage of a hotel shuttle bus free of charge. It makes several stops along Michigan Avenue, including Water Tower Place. Other stops include Navy Pier and the Museum Campus.Travelers who want to stay connected access high-speed wireless Internet throughout hotel for a fee, or visit the 24-hour business center. Transportation O’Hare International Airport (16.1 mi/26 km) Chicago Midway Airport (8.7 mi/14.1 km) Blue Line (LaSalle to O’Hare) (3.8 mi/6.1 km) Orange Line (Roosevelt to Midway) (0.3 mi/0.5 km) McCormick Place Convention Center (1.5 mi/2.3 km) Nearby attractions Grant Park (0.5 mi/0.9 km)Millennium Park (0.8 mi/1.3 km)Lake Michigan (1.4 mi/2.2 km)The Magnificent Mile (1.5 mi/2.5 km)Museum Campus (3.1 mi/5 km) Business Six meeting rooms with space for 12 for 125 guests 24-hour business center with desktop computers, high-speed Internet access (fees apply) and a printer Complimentary high-speed wireless Internet available throughout Chicago's Essex Inn Policies and feesParking fee is $50 USD per night.
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Nightly rates from $56

The Talbott Hotel

4 stars
4.6 / 5 1256 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.
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Nightly rates from $124

Congress Plaza Hotel at Grant Park

3 stars
3.3 / 5 1167 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.
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Nightly rates from $69

Inn of Chicago, an Ascend Collection hotel

3 stars
3.4 / 5 253 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 $59

The Silversmith Hotel Chicago

3 stars
4.2 / 5 237 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 $109
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Cheap Flights
Departure Arrival Travel dates Round-trip
New York Chicago Sat, Feb 7 - Tue, Feb 10 $87
Los Angeles Chicago Tue, Mar 17 - Wed, Mar 18 $237
Washington DC Chicago Mon, Mar 16 - Wed, Mar 18 $127
San Francisco Chicago Tue, Mar 24 - Wed, Mar 25 $245
Newark Chicago Mon, Mar 30 - Tue, Mar 31 $199
Atlanta Chicago Tue, Mar 3 - Wed, Mar 4 $107
Seattle Chicago Tue, Mar 10 - Mon, Mar 23 $282
Boston Chicago Mon, Feb 9 - Tue, Feb 10 $140
Dallas Chicago Tue, Mar 3 - Sat, Mar 7 $81
Denver Chicago Wed, Mar 11 - Tue, Mar 17 $119
Phoenix Chicago Tue, Mar 3 - Mon, Mar 9 $117
Orlando Chicago Tue, Mar 17 - Thu, Mar 19 $167
San Juan Chicago Wed, Mar 18 - Tue, Mar 31 $359
Mexico City Chicago Tue, Feb 3 - Mon, Feb 23 $336
Philadelphia Chicago Tue, Mar 17 - Wed, Mar 18 $200
San Diego Chicago Tue, Mar 24 - Tue, Apr 21 $263
Fort Lauderdale Chicago Wed, Feb 18 - Tue, Mar 3 $137
Las Vegas Chicago Wed, Feb 25 - Mon, Mar 2 $137
Guadalajara Chicago Wed, Mar 25 - Tue, Apr 7 $391
Tampa Chicago Tue, Mar 3 - Tue, Mar 10 $118
Houston Chicago Sat, Feb 7 - Tue, Feb 10 $115
Baltimore Chicago Tue, Feb 10 - Tue, Feb 17 $117
Honolulu Chicago Thu, Feb 19 - Wed, Mar 4 $673
Orange County Chicago Tue, Feb 17 - Wed, Feb 25 $272
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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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