Search Cheap Flights to
Chicago

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Chicago Flights as Low as $149

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Delta
Wed, Aug 19 - Tue, Sep 8
BOS
Logan Intl.
ORD
O'Hare Intl.
$149 Roundtrip, found 3 days ago
$149
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Aug 19 from Logan Intl. to O'Hare Intl., returning Tue, Sep 8, priced at $149 found 3 days ago
United
Tue, Aug 4 - Tue, Aug 11
BOS
Logan Intl.
ORD
O'Hare Intl.
$153 Roundtrip, found 18 hours ago
$153
Roundtrip
found 18 hours ago
Select United flight, departing Tue, Aug 4 from Logan Intl. to O'Hare Intl., returning Tue, Aug 11, priced at $153 found 18 hours ago
Delta
Wed, Aug 19 - Sun, Sep 6
BOS
Logan Intl.
ORD
O'Hare Intl.
$157 Roundtrip, found 3 days ago
$157
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Aug 19 from Logan Intl. to O'Hare Intl., returning Sun, Sep 6, priced at $157 found 3 days ago
American Airlines
Tue, Aug 4 - Tue, Aug 11
BOS
Logan Intl.
ORD
O'Hare Intl.
$163 Roundtrip, found 18 hours ago
$163
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Tue, Aug 4 from Logan Intl. to O'Hare Intl., returning Tue, Aug 11, priced at $163 found 18 hours ago
JetBlue Airways
Wed, Aug 12 - Sat, Aug 22
BOS
Logan Intl.
ORD
O'Hare Intl.
$173 Roundtrip, just found
$173
Roundtrip
just found
Select JetBlue Airways flight, departing Wed, Aug 12 from Logan Intl. to O'Hare Intl., returning Sat, Aug 22, priced at $173 just found
American Airlines
Tue, Jun 30 - Tue, Aug 4
BOS
Logan Intl.
RFD
Greater Rockford
$174 Roundtrip, found 3 days ago
$174
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Jun 30 from Logan Intl. to Greater Rockford, returning Tue, Aug 4, priced at $174 found 3 days ago
Frontier Airlines
Tue, Aug 25 - Tue, Sep 1
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$206 Roundtrip, found 3 days ago
$206
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Aug 25 from Los Angeles Intl. to O'Hare Intl., returning Tue, Sep 1, priced at $206 found 3 days ago
Frontier Airlines
Tue, Aug 18 - Wed, Sep 9
LAX
Los Angeles Intl.
MDW
Midway Intl.
$240 Roundtrip, found 16 hours ago
$240
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Tue, Aug 18 from Los Angeles Intl. to Midway Intl., returning Wed, Sep 9, priced at $240 found 16 hours ago
Frontier Airlines
Thu, Jul 30 - Tue, Aug 18
BOS
Logan Intl.
MDW
Midway Intl.
$242 Roundtrip, found 18 hours ago
$242
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Thu, Jul 30 from Logan Intl. to Midway Intl., returning Tue, Aug 18, priced at $242 found 18 hours ago
Bargain Flight
Fri, Jul 3 - Fri, Jul 10
SAN
San Diego Intl.
ORD
O'Hare Intl.
$271 Roundtrip, found 1 day ago
$271
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Fri, Jul 3 from San Diego Intl. to O'Hare Intl., returning Fri, Jul 10, priced at $271 found 1 day ago
Alaska Airlines
Tue, Oct 13 - Sat, Oct 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$315 Roundtrip, found 2 days ago
$315
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Tue, Oct 13 from Los Angeles Intl. to O'Hare Intl., returning Sat, Oct 17, priced at $315 found 2 days ago
American Airlines
Sat, Jul 18 - Sat, Jul 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$332 Roundtrip, found 1 day ago
$332
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Jul 18 from Los Angeles Intl. to Greater Rockford, returning Sat, Jul 25, priced at $332 found 1 day ago
Delta
Fri, Jul 24 - Thu, Jul 30
SAN
San Diego Intl.
MDW
Midway Intl.
$386 Roundtrip, found 5 days ago
$386
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Jul 24 from San Diego Intl. to Midway Intl., returning Thu, Jul 30, priced at $386 found 5 days ago
United
Fri, Jul 3 - Fri, Jul 10
CLD
McClellan-Palomar
ORD
O'Hare Intl.
$429 Roundtrip, found 18 hours ago
$429
Roundtrip
found 18 hours ago
Select United flight, departing Fri, Jul 3 from McClellan-Palomar to O'Hare Intl., returning Fri, Jul 10, priced at $429 found 18 hours ago
Sun Country Airlines
Wed, Jul 1 - Fri, Jul 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$563 Roundtrip, found 7 hours ago
$563
Roundtrip
found 7 hours ago
Select Sun Country Airlines flight, departing Wed, Jul 1 from Los Angeles Intl. to O'Hare Intl., returning Fri, Jul 3, priced at $563 found 7 hours ago
United
Fri, Jul 24 - Tue, Aug 4
CLD
McClellan-Palomar
MDW
Midway Intl.
$1,561 Roundtrip, found 18 hours ago
$1,561
Roundtrip
found 18 hours ago
Select United flight, departing Fri, Jul 24 from McClellan-Palomar to Midway Intl., returning Tue, Aug 4, priced at $1,561 found 18 hours ago

Cheap Flights to Chicago

Fall in love at first flight with your vacation to Chicago by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Chicago on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Chicago, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Chicago

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Chicago with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the CHI airport.

What is the cheapest month to fly to Chicago?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Chicago are in August, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Chicago?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 15 to choose from for your flight to Chicago.

What airport is best to fly into Chicago?

When you’re planning your trip to Chicago, convenience is the name of the game. Luckily, Chicago Midway Intl. Airport is nearby so you can deplane and get going on checking off everything on your Chicago must-do list.

How much are flights to Chicago?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chicago on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $149, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Chicago?

The trick to saving a stack of cash on your flight to Chicago? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $149 right now, why wait?

Chicago Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$108

Last Minute Hotel Deals in Chicago

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (10,128 reviews)
"Hotel has been updated some since our last stay. We have stayed here every summer in june for 6 years now. Its at the end of the strip, its a great price range, and it has all that we need. Staff is very nice. The bell hop guys are helpful and hilarious. Beds are comfortable. We will always choose ..."

Reviewed on Jun 18, 2026

Get rates
Congress Plaza Hotel
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,664 reviews)
"Hotel main trash service pickup was directly below my room window and was extremely loud when unloading and loading rolloff dumpsters at 4am. No way to sleep through the noise. Shuttle service was very good to and from the airport. Toilet clogged after one use with no plunger available. Remodeling ..."

Reviewed on Jun 17, 2026

Get rates
Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
Get rates
The Chicago Hotel Collection - Magnificent Mile
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.4/10 Very Good! (2,351 reviews)
"So convenient to the airport — an easy walk to terminal 2 and short train ride to the other terminals. No stress before an early morning flight. Great gym and pretty good casual restaurant. Clean and comfortable rooms."

Reviewed on Jun 16, 2026

Get rates
Hilton Chicago O'Hare Airport
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8.2/10 Very Good! (1,610 reviews)
"Clean room. Helpful staff, happy hour tickets, valet parking"

Reviewed on Jun 18, 2026

Get rates
The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
9/10 Wonderful! (4,439 reviews)
"Great central location. Beautiful views"

Reviewed on Jun 18, 2026

Get rates
Hilton Chicago/Magnificent Mile Suites
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue Chicago IL
Book a stay at this family-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise ...
8.6/10 Excellent! (3,011 reviews)
"Check in was prompt and the room was very clean."

Reviewed on Jun 18, 2026

Get rates
Warwick Allerton - Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
7.6/10 Good! (2,609 reviews)
"Honestly this was an amazing find for a downtown Chicago stay. If you’re super picky about how the room looks and want something modern, this isn’t for you. If you want a great location, helpful staff, affordable rates, and sound proof walls, then this is your place."

Reviewed on Jun 18, 2026

Get rates
Travelodge by Wyndham Downtown Chicago
See all 5,560 properties in Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Hotels With Free Airport Shuttle

Super 8 by Wyndham Chicago O'Hare Airport

Super 8 by Wyndham Chicago O'Hare Airport

3.5 out of 5
2951 Touhy Ave Elk Grove Village IL
Book a stay at this business-friendly hotel in Elk Grove Village. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
7.6/10 Good! (1,710 reviews)
"It was quiet and just what I needed"

Reviewed on Jun 18, 2026

Get rates
Super 8 by Wyndham Chicago O'Hare Airport
Country Inn & Suites by Radisson, Chicago O'Hare South, IL

Country Inn & Suites by Radisson, Chicago O'Hare South, IL

3 out of 5
777 E Grand Avenue Bensenville IL
Book a stay at this golf hotel in Bensenville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
7.6/10 Good! (1,520 reviews)
"good place to stay!! good breakfast selection"

Reviewed on Jun 18, 2026

Get rates
Country Inn & Suites by Radisson, Chicago O'Hare South, IL
Hampton Inn Chicago-O'Hare International Airport

Hampton Inn Chicago-O'Hare International Airport

2.5 out of 5
3939 N Mannheim Rd Schiller Park IL
Book a stay at this business-friendly hotel in Schiller Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (2,342 reviews)
"Very nice room with comfortable bed, sitting area and ample room for storage. Bathroom amenities were great but shower pressure could have been a bit stronger. Staff were very pleasant and helpful with a quick check in and out. Pool and fitness center were a plus. Our coffee pot in the room wasn't ..."

Reviewed on Jun 17, 2026

Get rates
Hampton Inn Chicago-O'Hare International Airport
Holiday Inn Chicago O'Hare Area by IHG

Holiday Inn Chicago O'Hare Area by IHG

3 out of 5
5615 North Cumberland Avenue Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
8.2/10 Very Good! (1,003 reviews)
"Everything was excellent, starting with the front desk, thank you"

Reviewed on Jun 18, 2026

Get rates
Holiday Inn Chicago O'Hare Area by IHG
Loews Chicago O'Hare Hotel

Loews Chicago O'Hare Hotel

4.5 out of 5
5300 N River Rd Rosemont IL
Book a stay at this luxury hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the restaurant and the helpful ...
9.4/10 Exceptional! (2,082 reviews)
"The room was very clean, bed was very comfortable. This is by far the best hotel I’ve stayed in."

Reviewed on Jun 15, 2026

Get rates
Loews Chicago O'Hare Hotel
Carlton Inn Midway

Carlton Inn Midway

2 out of 5
4944 S Archer Ave Chicago IL
Book a stay at this business-friendly motel in Chicago. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
6.2/10 (1,001 reviews)
"Kinda what you would expect from a motel, however we found left over food in our room"

Reviewed on Jun 14, 2026

Get rates
Carlton Inn Midway
See all 5,560 properties in Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.