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

Congress Plaza Hotel at Grant Park

3 stars
3.3 / 5 1097 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 Save 10% on your stay
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $125

Inn of Chicago, an Ascend Collection hotel

3 stars
3.3 / 5 222 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.
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $126

Club Quarters Central Loop

3 stars
4.1 / 5 533 reviews
Business traveler headquarters in Chicago's LoopThe Club Quarters Central Loop hotel might be mistaken for an office building with its subdued presence. A black awning marks this discrete spot and lends a sense of privacy. The hotel targets business travelers whose work brings them to the financial district and plays host to leisure travelers who want easy access to downtown attractions. Guests find great value for the location, price and attentive service, including a 24-hour concierge. The Club Quarters Central Loop hotel is within walking distance of several of Chicago's major attractions. Highlights Minutes from Michigan Avenue 24-hour concierge service Free high-speed wireless Internet throughout the hotel Elephant & Castle Pub and Restaurant next door RoomsThe clean and comfortable rooms at the Club Quarters Central Loop hotel keep the professional’s needs in mind. Ergonomic chairs and task lighting ease late work nights, while pillow-top mattress dressed in premium linens promise a refreshing night of sleep. Bookshelves display dictionaries and almanacs for a welcome scholarly touch. All rooms have complimentary wireless Internet access. FeaturesThe amenities at the Club Quarters Central Loop hotel are designed to keep guests productive. Find free high-speed wireless Internet access throughout the hotel, free use of a computer and printer, and five meeting rooms. Travelers looking to relax visit the restaurant and bar next door, exercise in the fitness room or lounge in the Private Club Room (Club Quarters members only) with complimentary coffee, tea, newspapers, magazines and games.Free, chilled bottled water is available on each floor. Transportation O’Hare International Airport (15.6 mi/25.1 km) Midway Airport (8.9 mi/14.3 km) Blue Line (Jackson/Dearborn) (0.1 mi/0.2 km) Orange Line (Quincy/Wells) (0.1 mi/0.2 km) McCormick Place Convention Center (2.1 mi/3.3 km) Attractions Board of Trade (0.1 mi/0.2 km) Theater district (0.2 mi/0.3 km) Willis (formerly Sears) Tower (0.2 mi/0.4 km) Symphony Center (0.3 mi/0.5 km) Chicago Mercantile Exchange (0.3 mi/0.5 km) The Art Institute of Chicago (0.4 mi/0.6 km)
Value Rate includes up to 10% off
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $89

Hampton Inn Majestic Chicago Theatre District

3 stars
4.3 / 5 84 reviews
Comfort and sophistication in a cultural settingThe Hampton Inn Majestic Chicago Theater District is situated above the Bank of America Theater, which has hosted productions by a number of celebrities, including Billy Joel. The convenient location in the heart of the theater district provides guests with easy access to some of the most fascinating cultural attractions in Chicago. On the hotel premises there is a wide range of amenities and services, including its signature hot breakfast. The Hampton Inn Majestic Chicago Theater District also features a 24-hour business and fitness center.  3 Reasons To Stay:Situated above the Bank of America TheaterFree wireless high-speed InternetComplimentary hot breakfast Hampton Inn Majestic Chicago Theater District RoomsRooms at the Hampton Inn Majestic Chicago Theater District offer a charming historic feel with extensive modern amenities. They are divided into standard and executive guest rooms, which are each equipped with a 32-inch high-definition TV with pay-per-view movies. Complimentary services and amenities such as wireless high-speed Internet and toiletries are included in every room. Complimentary tea and coffee are provided in standard guest rooms and executive rooms have refrigerators and microwaves. All types of accommodations are spacious, with executive rooms offering an extra living room area for guests traveling with family. Travelers to the city on business are provided with a selection of convenient amenities such as free telephone calls, a fax machine and large work desk. The hotel operates a nonsmoking policy and wheelchair access is provided for guests with disabilities. A housekeeping service is included with every room.  Things To Do:Shopping on State Street (0.1 mi/0.2 km)Millennium Park (0.3 mi/0.6 km)The Art Institute of Chicago Museum (0.4 mi/0.7 km)Grant Park (0.7 mi/1.2 km)Water Tower Place (1.6 mi/2.5 km)Navy Pier (1.7 mi/2.7 km) Policies and feesSmoke-free policy
Value Free On The HouseT hot breakfast, Wi-Fi
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $179

DoubleTree by Hilton Hotel Chicago - Magnificent Mile

3 stars
3.9 / 5 206 reviews
Windy City style and a side of hospitality with cookies at check-in When guests are torn between shopping and sightseeing, this Streeterville hotel answers the call with its convenient location near the Magnificent Mile and Navy Pier. Situated in the middle of both landmarks, Doubletree Hotel Chicago Magnificent Mile is a popular choice for families. Ample meeting rooms lure event planners with 16,000 square feet of event space.  Einstein Bros Bagels is onsite, as well as Markethouse, taking its inspiration from the Heartland: All ingredients are seasonal and locally sourced. Highlights Walk to Navy Pier and the Magnificent MileMarkethouse restaurant features seasonal fare16,000 square feet of event spaceOutdoor pool, sundeck and H2O bar open in summerWarm chocolate chip cookies at check-in RoomsSpacious rooms at Doubletree Hotel Chicago Magnificent Mile stick to a chic palette of red, mahogany and gray. Guests sleep on signature Doubletree Sweet Dreams mattresses topped with white linens and shiny rouge coverlets. Windows frame city or lake views, partial or full depending on the room. Standard rooms attend to the basics, from flat-screen TVs to Wolfgang Puck coffee and tea. Wireless Internet can be accessed for a charge. DiningLocalvores will appreciate the use of organic, locally-sourced produce and meat at Markethouse, one of two dining options at the Doubletree Hotel Chicago Magnificent Mile. While the farmhouse chic space could qualify as fine dining, the menu is approachable, boasting classics such as meatloaf, angus burgers and half-chicken fired in the rotisserie. On the run? Take a bagel break at Einstein Bros Bagels, which serves hot, fresh bagels alongside breakfast wraps, sandwiches and salads. Transportation O'Hare International Airport (17 miles)Midway Airport (12 miles)Closest train stops: Blue Line (Chicago to O'Hare) and Orange Line (Roosevelt to Midway)McCormick Place Convention Center (10 minutes) Business 16,000 square feet of meeting space, including a 6,700-square-foot ballroom and one floor dedicated to breakout rooms 24-hour business center with workstation, color printing and copyingFree Wi-Fi in lobbyWi-Fi in rooms (fees apply)
Value Signature chocolate chip cookie at check-in
Flight + Hotel
Book a package for more savings!
Hotel only
Nightly rates from $179
Back to menu Return to top

Cheap Flights
Departure Arrival Travel dates Round-trip
New York Chicago Mon, Nov 17 - Tue, Nov 18 $182
Los Angeles Chicago Sat, Oct 18 - Wed, Oct 22 $275
Washington DC Chicago Fri, Oct 17 - Fri, Oct 24 $155
San Francisco Chicago Thu, Nov 27 - Tue, Dec 2 $265
Newark Chicago Tue, Oct 28 - Fri, Oct 31 $258
Atlanta Chicago Fri, Oct 24 - Tue, Oct 28 $115
Seattle Chicago Fri, Nov 7 - Wed, Nov 12 $299
Boston Chicago Wed, Oct 29 - Sat, Nov 1 $115
Dallas Chicago Wed, Oct 15 - Tue, Oct 21 $115
Denver Chicago Tue, Oct 28 - Wed, Nov 5 $135
Phoenix Chicago Thu, Nov 20 - Tue, Dec 2 $190
Orlando Chicago Mon, Nov 3 - Tue, Nov 11 $177
San Juan Chicago Wed, Nov 5 - Sun, Nov 9 $281
Mexico City Chicago Fri, Oct 31 - Fri, Nov 7 $344
Philadelphia Chicago Tue, Nov 4 - Sat, Nov 8 $276
San Diego Chicago Wed, Oct 22 - Sat, Oct 25 $299
Fort Lauderdale Chicago Wed, Oct 15 - Tue, Oct 28 $225
Las Vegas Chicago Tue, Oct 14 - Wed, Oct 15 $193
Guadalajara Chicago Mon, Nov 24 - Mon, Dec 1 $508
Tampa Chicago Sat, Nov 15 - Tue, Nov 18 $215
Houston Chicago Wed, Oct 15 - Tue, Oct 21 $173
Baltimore Chicago Wed, Oct 15 - Sat, Oct 18 $165
Honolulu Chicago Mon, Nov 3 - Tue, Nov 11 $652
Orange County Chicago Fri, Oct 31 - Tue, Nov 4 $317
Back to menu Return to top

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.

Your trip

Hotel options

Hotel stay must be within date range of Leave and Return.

Room 1
Age categories
Ages of children at time of trip (for pricing, discounts)